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

Bruce P. Branchaud; Mark S. Meier

doi:10.1016/0040-4039(88)85118-9

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

Bruce P. Branchaud, Mark S. Meier

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

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 language	English (US)
Pages (from-to)	3191-3194
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	26
DOIs	https://doi.org/10.1016/0040-4039(88)85118-9
State	Published - 1988
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/0040-4039(88)85118-9

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 = "Branchaud, {Bruce P.} and Meier, {Mark S.}",

year = "1988",

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 P.

AU - Meier, Mark S.

PY - 1988

Y1 - 1988

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

SN - 0040-4039

VL - 29

SP - 3191

EP - 3194

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this