A Ramberg-Backlund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

D E  Paterson; F K  Griffin; M L  Alcaraz; R J K  Taylor

A Ramberg-Backlund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

D E Paterson, F K Griffin, M L Alcaraz, R J K Taylor

Chemistry

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

Abstract

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Backlund rearrangement, are described. These include a formal synthesis of a beta-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Backlund rearrangement is also reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Original language	English
Pages (from-to)	1323-1336
Number of pages	14
Journal	European Journal of Organic Chemistry
Issue number	7
Publication status	Published - Apr 2002

Keywords

carbohydrates
sulfones
rearrangements
exo-glycals
STEREOSELECTIVE SYNTHESIS
OLEFIN METATHESIS
EXO-GLYCALS
PREFERRED CONFORMATION
L-SERINE
ANALOG
CONVERGENT
INHIBITORS
SUGARS
ROUTE

Cite this

@article{e50e8402a8964a609bef57b1c8b1b364,

title = "A Ramberg-Backlund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids",

abstract = "Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Backlund rearrangement, are described. These include a formal synthesis of a beta-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Backlund rearrangement is also reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).",

keywords = "carbohydrates, sulfones, rearrangements, exo-glycals, STEREOSELECTIVE SYNTHESIS, OLEFIN METATHESIS, EXO-GLYCALS, PREFERRED CONFORMATION, L-SERINE, ANALOG, CONVERGENT, INHIBITORS, SUGARS, ROUTE",

author = "Paterson, {D E} and Griffin, {F K} and Alcaraz, {M L} and Taylor, {R J K}",

year = "2002",

month = apr,

language = "English",

pages = "1323--1336",

journal = "European Journal of Organic Chemistry",

issn = "1099-0690",

publisher = "Wiley-Blackwell",

number = "7",

}

TY - JOUR

T1 - A Ramberg-Backlund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

AU - Paterson, D E

AU - Griffin, F K

AU - Alcaraz, M L

AU - Taylor, R J K

PY - 2002/4

Y1 - 2002/4

N2 - Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Backlund rearrangement, are described. These include a formal synthesis of a beta-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Backlund rearrangement is also reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

AB - Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Backlund rearrangement, are described. These include a formal synthesis of a beta-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Backlund rearrangement is also reported. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

KW - carbohydrates

KW - sulfones

KW - rearrangements

KW - exo-glycals

KW - STEREOSELECTIVE SYNTHESIS

KW - OLEFIN METATHESIS

KW - EXO-GLYCALS

KW - PREFERRED CONFORMATION

KW - L-SERINE

KW - ANALOG

KW - CONVERGENT

KW - INHIBITORS

KW - SUGARS

KW - ROUTE

M3 - Article

SN - 1099-0690

SP - 1323

EP - 1336

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -