A synthesis of ammonium 3-deoxy-(d)-manno-2-octulosonate (ammonium kdo) from (d)-mannose via cobaloxime-mediated radical alkyl-alkenyl cross coupling

Bruce Branchaud, Mark S. Meier

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-(d)-manno-2-octulosonic acid (KDO) starting from (d)-mannose. The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxime mediated radical alkyl-alkenyl cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose. KMnO4 unmasking of the latent functionality in the α-ethoxyacrylonitrile moiety provides the α-hydroxyester moiety necessary for completion of the KDO synthesis.

Original languageEnglish (US)
Pages (from-to)3191-3194
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number26
DOIs
StatePublished - Jan 1 1988
Externally publishedYes

Fingerprint

Mannose
Ammonium Compounds
Monosaccharides
Carbon
Salts
Derivatives
cobaloxime
2-octulosonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{5a873f1671be4ffb9411407e2bf4abb1,
title = "A synthesis of ammonium 3-deoxy-(d)-manno-2-octulosonate (ammonium kdo) from (d)-mannose via cobaloxime-mediated radical alkyl-alkenyl cross coupling",
abstract = "We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-(d)-manno-2-octulosonic acid (KDO) starting from (d)-mannose. The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxime mediated radical alkyl-alkenyl cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose. KMnO4 unmasking of the latent functionality in the α-ethoxyacrylonitrile moiety provides the α-hydroxyester moiety necessary for completion of the KDO synthesis.",
author = "Bruce Branchaud and Meier, {Mark S.}",
year = "1988",
month = "1",
day = "1",
doi = "10.1016/0040-4039(88)85118-9",
language = "English (US)",
volume = "29",
pages = "3191--3194",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "26",

}

TY - JOUR

T1 - A synthesis of ammonium 3-deoxy-(d)-manno-2-octulosonate (ammonium kdo) from (d)-mannose via cobaloxime-mediated radical alkyl-alkenyl cross coupling

AU - Branchaud, Bruce

AU - Meier, Mark S.

PY - 1988/1/1

Y1 - 1988/1/1

N2 - We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-(d)-manno-2-octulosonic acid (KDO) starting from (d)-mannose. The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxime mediated radical alkyl-alkenyl cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose. KMnO4 unmasking of the latent functionality in the α-ethoxyacrylonitrile moiety provides the α-hydroxyester moiety necessary for completion of the KDO synthesis.

AB - We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-(d)-manno-2-octulosonic acid (KDO) starting from (d)-mannose. The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxime mediated radical alkyl-alkenyl cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose. KMnO4 unmasking of the latent functionality in the α-ethoxyacrylonitrile moiety provides the α-hydroxyester moiety necessary for completion of the KDO synthesis.

UR - http://www.scopus.com/inward/record.url?scp=0023881722&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023881722&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(88)85118-9

DO - 10.1016/0040-4039(88)85118-9

M3 - Article

AN - SCOPUS:0023881722

VL - 29

SP - 3191

EP - 3194

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 26

ER -