Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides

Steen Uldall Hansen; Marek Baráth; Bader A B Salameh; Robin G. Pritchard; William T. Stimpson; John M. Gardiner; Gordon C. Jayson

doi:10.1021/ol901723m

Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides

Steen Uldall Hansen, Marek Baráth, Bader A B Salameh, Robin G. Pritchard, William T. Stimpson, John M. Gardiner, Gordon C. Jayson

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

Abstract

L-ldo cyanohydrln 3 was prepared from dlacetone-D-glucose In four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-Ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-Isopropylldineprotected L-ldo nitrile (8), lduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamlde) of heparin-related disaccharides. © 2009 American Chemical Society.

Original language	English
Pages (from-to)	4528-4531
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	20
DOIs	https://doi.org/10.1021/ol901723m
Publication status	Published - 15 Oct 2009

Keywords

Air
Disaccharides/*chemical synthesis/*chemistry
Heparin/*chemistry
Iduronic Acid/*analogs & derivatives/*chemical synthesis
Indicators and Reagents/chemistry
Nitriles/*chemistry
Stereoisomerism
Substrate Specificity
Temperature

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10.1021/ol901723m

CCDC 736690: Experimental Crystal Structure Determination
Hansen, S. U. (Contributor), Baráth, M. (Contributor), Salameh, B. A. B. (Contributor), Pritchard, R. (Contributor), Stimpson, W. T. (Contributor), Gardiner, J. (Contributor) & Jayson, G. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccsql68, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccsql68&sid=DataCite
Dataset

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title = "Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides",

abstract = "L-ldo cyanohydrln 3 was prepared from dlacetone-D-glucose In four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-Ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-Isopropylldineprotected L-ldo nitrile (8), lduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamlde) of heparin-related disaccharides. {\textcopyright} 2009 American Chemical Society.",

keywords = "Air, Disaccharides/*chemical synthesis/*chemistry, Heparin/*chemistry, Iduronic Acid/*analogs & derivatives/*chemical synthesis, Indicators and Reagents/chemistry, Nitriles/*chemistry, Stereoisomerism, Substrate Specificity, Temperature",

author = "Hansen, {Steen Uldall} and Marek Bar{\'a}th and Salameh, {Bader A B} and Pritchard, {Robin G.} and Stimpson, {William T.} and Gardiner, {John M.} and Jayson, {Gordon C.}",

note = "Times Cited: 3",

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day = "15",

doi = "10.1021/ol901723m",

language = "English",

volume = "11",

pages = "4528--4531",

journal = "Organic Letters",

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T1 - Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides

AU - Hansen, Steen Uldall

AU - Baráth, Marek

AU - Salameh, Bader A B

AU - Pritchard, Robin G.

AU - Stimpson, William T.

AU - Gardiner, John M.

AU - Jayson, Gordon C.

N1 - Times Cited: 3

PY - 2009/10/15

Y1 - 2009/10/15

N2 - L-ldo cyanohydrln 3 was prepared from dlacetone-D-glucose In four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-Ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-Isopropylldineprotected L-ldo nitrile (8), lduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamlde) of heparin-related disaccharides. © 2009 American Chemical Society.

AB - L-ldo cyanohydrln 3 was prepared from dlacetone-D-glucose In four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-Ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-Isopropylldineprotected L-ldo nitrile (8), lduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamlde) of heparin-related disaccharides. © 2009 American Chemical Society.

KW - Air

KW - Disaccharides/chemical synthesis/chemistry

KW - Heparin/chemistry

KW - Iduronic Acid/analogs & derivatives/chemical synthesis

KW - Indicators and Reagents/chemistry

KW - Nitriles/chemistry

KW - Stereoisomerism

KW - Substrate Specificity

KW - Temperature

U2 - 10.1021/ol901723m

DO - 10.1021/ol901723m

M3 - Article

SN - 1523-7052

VL - 11

SP - 4528

EP - 4531

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides

Abstract

Keywords

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Datasets

CCDC 736690: Experimental Crystal Structure Determination

Cite this