Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2003-06

AUTHORS

L. O. Kononov, A. M. Shpirt, Y. Ito, T. Ogawa

ABSTRACT

Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl thioglycoside (LiI, Py, reflux) proceeded inefficiently in contrast to the analogous smooth reaction of phenyl thioglycoside. An indirect route to derivatives with a free carboxy group involving saponification followed by acetylation of hydroxy groups proved to be more efficient for methyl α-thioglycoside of Neu5Ac. More... »

PAGES

1442-1446

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1024855917480

DOI

http://dx.doi.org/10.1023/a:1024855917480

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1009841942


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0305", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Organic Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Russian Academy of Sciences", 
          "id": "https://www.grid.ac/institutes/grid.4886.2", 
          "name": [
            "N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Kononov", 
        "givenName": "L. O.", 
        "id": "sg:person.0664126006.53", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.0664126006.53"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "Higher Chemical College of the Russian Academy of Sciences, 9 Miusskaya pl., 125047, Moscow, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Shpirt", 
        "givenName": "A. M.", 
        "id": "sg:person.01125434462.73", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01125434462.73"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "RIKEN", 
          "id": "https://www.grid.ac/institutes/grid.7597.c", 
          "name": [
            "Institute of Physical and Chemical Research (RIKEN), Hirosawa 2-1, 351-01, Wako-shi, Saitama, Japan"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Ito", 
        "givenName": "Y.", 
        "id": "sg:person.01224256473.75", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01224256473.75"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "RIKEN", 
          "id": "https://www.grid.ac/institutes/grid.7597.c", 
          "name": [
            "Institute of Physical and Chemical Research (RIKEN), Hirosawa 2-1, 351-01, Wako-shi, Saitama, Japan"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Ogawa", 
        "givenName": "T.", 
        "id": "sg:person.07766562153.43", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07766562153.43"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "https://doi.org/10.1016/0008-6215(89)80054-0", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1008902120"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1248/cpb.36.4678", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1029557874"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/cr990307k", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1054054305"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/cr990307k", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1054054305"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/cr990313g", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1054056989"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/cr990313g", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1054056989"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2003-06", 
    "datePublishedReg": "2003-06-01", 
    "description": "Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl thioglycoside (LiI, Py, reflux) proceeded inefficiently in contrast to the analogous smooth reaction of phenyl thioglycoside. An indirect route to derivatives with a free carboxy group involving saponification followed by acetylation of hydroxy groups proved to be more efficient for methyl \u03b1-thioglycoside of Neu5Ac.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1023/a:1024855917480", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1022309", 
        "issn": [
          "1066-5285", 
          "1573-9171"
        ], 
        "name": "Russian Chemical Bulletin", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "6", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "52"
      }
    ], 
    "name": "Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group", 
    "pagination": "1442-1446", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "2ee305a614e48ac313be2ab354dced74da6e46a46b646694126db278c1db3745"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1023/a:1024855917480"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1009841942"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1023/a:1024855917480", 
      "https://app.dimensions.ai/details/publication/pub.1009841942"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-10T21:41", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000001_0000000264/records_8687_00000536.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "http://link.springer.com/10.1023%2FA%3A1024855917480"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1023/a:1024855917480'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1023/a:1024855917480'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1023/a:1024855917480'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1023/a:1024855917480'


 

This table displays all metadata directly associated to this object as RDF triples.

99 TRIPLES      21 PREDICATES      31 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1023/a:1024855917480 schema:about anzsrc-for:03
2 anzsrc-for:0305
3 schema:author N0936f000bee24448b9f80fd38cfef147
4 schema:citation https://doi.org/10.1016/0008-6215(89)80054-0
5 https://doi.org/10.1021/cr990307k
6 https://doi.org/10.1021/cr990313g
7 https://doi.org/10.1248/cpb.36.4678
8 schema:datePublished 2003-06
9 schema:datePublishedReg 2003-06-01
10 schema:description Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl thioglycoside (LiI, Py, reflux) proceeded inefficiently in contrast to the analogous smooth reaction of phenyl thioglycoside. An indirect route to derivatives with a free carboxy group involving saponification followed by acetylation of hydroxy groups proved to be more efficient for methyl α-thioglycoside of Neu5Ac.
11 schema:genre research_article
12 schema:inLanguage en
13 schema:isAccessibleForFree false
14 schema:isPartOf Nc33e3ced94f845b1a1b7e841d297c96d
15 Nf41876f7d47f4d8fa17e31df95b9b2fe
16 sg:journal.1022309
17 schema:name Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group
18 schema:pagination 1442-1446
19 schema:productId N2075195968b3470f96c228194c9c206e
20 N7144163d018e4bb7912d08f565a2305a
21 N77c454982ffc4c37989344c8f9f8eb0e
22 schema:sameAs https://app.dimensions.ai/details/publication/pub.1009841942
23 https://doi.org/10.1023/a:1024855917480
24 schema:sdDatePublished 2019-04-10T21:41
25 schema:sdLicense https://scigraph.springernature.com/explorer/license/
26 schema:sdPublisher N8db8909821dd493db1f2e6d2e1c13674
27 schema:url http://link.springer.com/10.1023%2FA%3A1024855917480
28 sgo:license sg:explorer/license/
29 sgo:sdDataset articles
30 rdf:type schema:ScholarlyArticle
31 N0365d4bdb30c49f49a62160b6cde8af4 schema:name Higher Chemical College of the Russian Academy of Sciences, 9 Miusskaya pl., 125047, Moscow, Russian Federation
32 rdf:type schema:Organization
33 N0936f000bee24448b9f80fd38cfef147 rdf:first sg:person.0664126006.53
34 rdf:rest N8f1457708a1040109a92a0a08c2b25cb
35 N2075195968b3470f96c228194c9c206e schema:name dimensions_id
36 schema:value pub.1009841942
37 rdf:type schema:PropertyValue
38 N63e225360cc04c71adb77c05f356cbd7 rdf:first sg:person.01224256473.75
39 rdf:rest Nf864e9ee0fd34914a61efb51ab80cfc1
40 N7144163d018e4bb7912d08f565a2305a schema:name readcube_id
41 schema:value 2ee305a614e48ac313be2ab354dced74da6e46a46b646694126db278c1db3745
42 rdf:type schema:PropertyValue
43 N77c454982ffc4c37989344c8f9f8eb0e schema:name doi
44 schema:value 10.1023/a:1024855917480
45 rdf:type schema:PropertyValue
46 N8db8909821dd493db1f2e6d2e1c13674 schema:name Springer Nature - SN SciGraph project
47 rdf:type schema:Organization
48 N8f1457708a1040109a92a0a08c2b25cb rdf:first sg:person.01125434462.73
49 rdf:rest N63e225360cc04c71adb77c05f356cbd7
50 Nc33e3ced94f845b1a1b7e841d297c96d schema:issueNumber 6
51 rdf:type schema:PublicationIssue
52 Nf41876f7d47f4d8fa17e31df95b9b2fe schema:volumeNumber 52
53 rdf:type schema:PublicationVolume
54 Nf864e9ee0fd34914a61efb51ab80cfc1 rdf:first sg:person.07766562153.43
55 rdf:rest rdf:nil
56 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
57 schema:name Chemical Sciences
58 rdf:type schema:DefinedTerm
59 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
60 schema:name Organic Chemistry
61 rdf:type schema:DefinedTerm
62 sg:journal.1022309 schema:issn 1066-5285
63 1573-9171
64 schema:name Russian Chemical Bulletin
65 rdf:type schema:Periodical
66 sg:person.01125434462.73 schema:affiliation N0365d4bdb30c49f49a62160b6cde8af4
67 schema:familyName Shpirt
68 schema:givenName A. M.
69 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01125434462.73
70 rdf:type schema:Person
71 sg:person.01224256473.75 schema:affiliation https://www.grid.ac/institutes/grid.7597.c
72 schema:familyName Ito
73 schema:givenName Y.
74 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01224256473.75
75 rdf:type schema:Person
76 sg:person.0664126006.53 schema:affiliation https://www.grid.ac/institutes/grid.4886.2
77 schema:familyName Kononov
78 schema:givenName L. O.
79 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.0664126006.53
80 rdf:type schema:Person
81 sg:person.07766562153.43 schema:affiliation https://www.grid.ac/institutes/grid.7597.c
82 schema:familyName Ogawa
83 schema:givenName T.
84 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07766562153.43
85 rdf:type schema:Person
86 https://doi.org/10.1016/0008-6215(89)80054-0 schema:sameAs https://app.dimensions.ai/details/publication/pub.1008902120
87 rdf:type schema:CreativeWork
88 https://doi.org/10.1021/cr990307k schema:sameAs https://app.dimensions.ai/details/publication/pub.1054054305
89 rdf:type schema:CreativeWork
90 https://doi.org/10.1021/cr990313g schema:sameAs https://app.dimensions.ai/details/publication/pub.1054056989
91 rdf:type schema:CreativeWork
92 https://doi.org/10.1248/cpb.36.4678 schema:sameAs https://app.dimensions.ai/details/publication/pub.1029557874
93 rdf:type schema:CreativeWork
94 https://www.grid.ac/institutes/grid.4886.2 schema:alternateName Russian Academy of Sciences
95 schema:name N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
96 rdf:type schema:Organization
97 https://www.grid.ac/institutes/grid.7597.c schema:alternateName RIKEN
98 schema:name Institute of Physical and Chemical Research (RIKEN), Hirosawa 2-1, 351-01, Wako-shi, Saitama, Japan
99 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...