Stereoselective synthesis of the α-glycoside of a KDO "C"-disaccharide

Mamoru Koketsu; Balagurunathan Kuberan; Robert J. Linhardt

doi:10.1021/ol006458n

Stereoselective synthesis of the α-glycoside of a KDO "C"-disaccharide

Mamoru Koketsu, Balagurunathan Kuberan, Robert J. Linhardt

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

25 Scopus citations

Abstract

(matrix presented) The reaction of tert-butyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl chloride)onate donor 7 with the 6-formylgalactopyranoside acceptor 4 in the presence of Sml₂ provided only the KDO α-C-disaccharide 8. The bulky tert-butyl ester in the donor was used to reverse the stereochemical outcome of C-glycosylation, stereoselectively forming the α-"C"-disaccharide of KDO.

Original language	English
Pages (from-to)	3361-3363
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	21
DOIs	https://doi.org/10.1021/ol006458n
State	Published - 19 Oct 2000
Externally published	Yes

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@article{662a393884274ab5baacc9bd71f9b6d1,

title = "Stereoselective synthesis of the α-glycoside of a KDO {"}C{"}-disaccharide",

abstract = "(matrix presented) The reaction of tert-butyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl chloride)onate donor 7 with the 6-formylgalactopyranoside acceptor 4 in the presence of Sml2 provided only the KDO α-C-disaccharide 8. The bulky tert-butyl ester in the donor was used to reverse the stereochemical outcome of C-glycosylation, stereoselectively forming the α-{"}C{"}-disaccharide of KDO.",

author = "Mamoru Koketsu and Balagurunathan Kuberan and Linhardt, {Robert J.}",

year = "2000",

month = oct,

day = "19",

doi = "10.1021/ol006458n",

language = "English",

volume = "2",

pages = "3361--3363",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

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TY - JOUR

T1 - Stereoselective synthesis of the α-glycoside of a KDO "C"-disaccharide

AU - Koketsu, Mamoru

AU - Kuberan, Balagurunathan

AU - Linhardt, Robert J.

PY - 2000/10/19

Y1 - 2000/10/19

N2 - (matrix presented) The reaction of tert-butyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl chloride)onate donor 7 with the 6-formylgalactopyranoside acceptor 4 in the presence of Sml2 provided only the KDO α-C-disaccharide 8. The bulky tert-butyl ester in the donor was used to reverse the stereochemical outcome of C-glycosylation, stereoselectively forming the α-"C"-disaccharide of KDO.

AB - (matrix presented) The reaction of tert-butyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl chloride)onate donor 7 with the 6-formylgalactopyranoside acceptor 4 in the presence of Sml2 provided only the KDO α-C-disaccharide 8. The bulky tert-butyl ester in the donor was used to reverse the stereochemical outcome of C-glycosylation, stereoselectively forming the α-"C"-disaccharide of KDO.

UR - http://www.scopus.com/inward/record.url?scp=0034687189&partnerID=8YFLogxK

U2 - 10.1021/ol006458n

DO - 10.1021/ol006458n

M3 - Article

C2 - 11029211

AN - SCOPUS:0034687189

SN - 1523-7060

VL - 2

SP - 3361

EP - 3363

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Stereoselective synthesis of the α-glycoside of a KDO "C"-disaccharide

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