Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters

Ivone Carvalho; Shona L. Scheuerl; K. P. Ravindranathan Kartha; Robert A. Field

doi:10.1016/S0008-6215(03)00071-5

Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters

Ivone Carvalho
, Shona L. Scheuerl
, K. P. Ravindranathan Kartha
, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

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

29 Citations (Scopus)

Abstract

Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).

Original language	English
Pages (from-to)	1039-1043
Number of pages	5
Journal	Carbohydrate Research
Volume	338
Issue number	10
Early online date	26 Mar 2003
DOIs	https://doi.org/10.1016/S0008-6215(03)00071-5
Publication status	Published - 1 May 2003

Keywords

Benzyl ester
Free carboxylic acid
Glycosylation
Mercuric bromide
Serine
Threonine

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10.1016/S0008-6215(03)00071-5

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title = "Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters",

abstract = "Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62\%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40\%, respectively).",

keywords = "Benzyl ester, Free carboxylic acid, Glycosylation, Mercuric bromide, Serine, Threonine",

author = "Ivone Carvalho and Scheuerl, \{Shona L.\} and Kartha, \{K. P. Ravindranathan\} and Field, \{Robert A.\}",

note = "Funding Information: These studies were supported by the MRC and the Weston Foundation. Support in the form of a research leave fellowship from FAPESP is gratefully acknowledged (IC). We thank Julia Bilke for performing some preliminary glycosylation experiments. We are indebted to the EPSRC Mass Spectrometry Service Centre, Swansea for invaluable support.",

year = "2003",

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doi = "10.1016/S0008-6215(03)00071-5",

language = "English",

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pages = "1039--1043",

journal = "Carbohydrate Research",

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TY - JOUR

T1 - Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters

AU - Carvalho, Ivone

AU - Scheuerl, Shona L.

AU - Kartha, K. P. Ravindranathan

AU - Field, Robert A.

N1 - Funding Information: These studies were supported by the MRC and the Weston Foundation. Support in the form of a research leave fellowship from FAPESP is gratefully acknowledged (IC). We thank Julia Bilke for performing some preliminary glycosylation experiments. We are indebted to the EPSRC Mass Spectrometry Service Centre, Swansea for invaluable support.

PY - 2003/5/1

Y1 - 2003/5/1

N2 - Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).

AB - Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).

KW - Benzyl ester

KW - Free carboxylic acid

KW - Glycosylation

KW - Mercuric bromide

KW - Serine

KW - Threonine

UR - https://www.scopus.com/pages/publications/0037403301

U2 - 10.1016/S0008-6215(03)00071-5

DO - 10.1016/S0008-6215(03)00071-5

M3 - Article

C2 - 12706969

AN - SCOPUS:0037403301

SN - 0008-6215

VL - 338

SP - 1039

EP - 1043

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 10

ER -

Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters

Abstract

Keywords

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