Synthesis of 3-deoxy-D-manno-octulosonic acid (KDO)

Peter M. Collins, W. George Overend, Tony Kung Ming Shing

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

2,3:5,6-Di-O-isopropylidene-D-mannose has been converted by five sequential reactions (Wittig reaction, deacetonation, hydrogenation, lactonisation, and isopropylidenation) into 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-octonolactone which in a Wasserman reaction gave an α-ketolactone from which KDO could readily be obtained by hydrolysis.

Original languageEnglish
Pages (from-to)1139-1140
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number21
DOIs
Publication statusPublished - 1981 Jan 1
Externally publishedYes

Fingerprint

Hydrogenation
Hydrolysis
Acids
Mannose
propylene
2-keto-3-deoxyoctonate

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis of 3-deoxy-D-manno-octulosonic acid (KDO). / Collins, Peter M.; Overend, W. George; Shing, Tony Kung Ming.

In: Journal of the Chemical Society, Chemical Communications, No. 21, 01.01.1981, p. 1139-1140.

Research output: Contribution to journalArticle

Collins, Peter M. ; Overend, W. George ; Shing, Tony Kung Ming. / Synthesis of 3-deoxy-D-manno-octulosonic acid (KDO). In: Journal of the Chemical Society, Chemical Communications. 1981 ; No. 21. pp. 1139-1140.
@article{1cdb6c561fff40e8bc0604a1c2a49cd0,
title = "Synthesis of 3-deoxy-D-manno-octulosonic acid (KDO)",
abstract = "2,3:5,6-Di-O-isopropylidene-D-mannose has been converted by five sequential reactions (Wittig reaction, deacetonation, hydrogenation, lactonisation, and isopropylidenation) into 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-octonolactone which in a Wasserman reaction gave an α-ketolactone from which KDO could readily be obtained by hydrolysis.",
author = "Collins, {Peter M.} and Overend, {W. George} and Shing, {Tony Kung Ming}",
year = "1981",
month = "1",
day = "1",
doi = "10.1039/C39810001139",
language = "English",
pages = "1139--1140",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "21",

}

TY - JOUR

T1 - Synthesis of 3-deoxy-D-manno-octulosonic acid (KDO)

AU - Collins, Peter M.

AU - Overend, W. George

AU - Shing, Tony Kung Ming

PY - 1981/1/1

Y1 - 1981/1/1

N2 - 2,3:5,6-Di-O-isopropylidene-D-mannose has been converted by five sequential reactions (Wittig reaction, deacetonation, hydrogenation, lactonisation, and isopropylidenation) into 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-octonolactone which in a Wasserman reaction gave an α-ketolactone from which KDO could readily be obtained by hydrolysis.

AB - 2,3:5,6-Di-O-isopropylidene-D-mannose has been converted by five sequential reactions (Wittig reaction, deacetonation, hydrogenation, lactonisation, and isopropylidenation) into 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-octonolactone which in a Wasserman reaction gave an α-ketolactone from which KDO could readily be obtained by hydrolysis.

UR - http://www.scopus.com/inward/record.url?scp=37049098866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049098866&partnerID=8YFLogxK

U2 - 10.1039/C39810001139

DO - 10.1039/C39810001139

M3 - Article

SP - 1139

EP - 1140

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 21

ER -