Glycosyl phosphites as glycosylation reagents

Shin Aoki, Hirosato Kondo, Chi Huey Wong

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

This chapter describes the application of glycosyl phosphites to the synthesis of different types of glycosides. The development of new methods for the efficient construction of glycosidic bonds is an objective of current research in carbohydrate synthesis. The practical and stereo controlled synthesis of oligosaccharides containing sialic acid, for example, remains of particular interest because of their important roles in biological recognition and cellular communication. However, the steric hindrance of the anomeric center and the ease of elimination during activation and glycosylation make the sialylation reaction particularly difficult to execute in a high-yield and stereoselective manner. A novel and high-yield sialylation using sialyl phosphite as donor and trimethylsilyltrifluoromethane sulfonate (TMSOTf) as catalyst has been illustrated in the chapter.

Original languageEnglish
Pages (from-to)193-211
Number of pages19
JournalMethods in enzymology
Volume247
Issue numberC
DOIs
Publication statusPublished - Jan 1 1994
Externally publishedYes

Fingerprint

Phosphites
Glycosylation
N-Acetylneuraminic Acid
Glycosides
Oligosaccharides
Cellular radio systems
Carbohydrates
Chemical activation
Research
Catalysts

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology

Cite this

Glycosyl phosphites as glycosylation reagents. / Aoki, Shin; Kondo, Hirosato; Wong, Chi Huey.

In: Methods in enzymology, Vol. 247, No. C, 01.01.1994, p. 193-211.

Research output: Contribution to journalArticle

Aoki, Shin ; Kondo, Hirosato ; Wong, Chi Huey. / Glycosyl phosphites as glycosylation reagents. In: Methods in enzymology. 1994 ; Vol. 247, No. C. pp. 193-211.
@article{c52019a91384429d8a0bc548890ced48,
title = "Glycosyl phosphites as glycosylation reagents",
abstract = "This chapter describes the application of glycosyl phosphites to the synthesis of different types of glycosides. The development of new methods for the efficient construction of glycosidic bonds is an objective of current research in carbohydrate synthesis. The practical and stereo controlled synthesis of oligosaccharides containing sialic acid, for example, remains of particular interest because of their important roles in biological recognition and cellular communication. However, the steric hindrance of the anomeric center and the ease of elimination during activation and glycosylation make the sialylation reaction particularly difficult to execute in a high-yield and stereoselective manner. A novel and high-yield sialylation using sialyl phosphite as donor and trimethylsilyltrifluoromethane sulfonate (TMSOTf) as catalyst has been illustrated in the chapter.",
author = "Shin Aoki and Hirosato Kondo and Wong, {Chi Huey}",
year = "1994",
month = "1",
day = "1",
doi = "10.1016/S0076-6879(94)47015-4",
language = "English",
volume = "247",
pages = "193--211",
journal = "Methods in Enzymology",
issn = "0076-6879",
publisher = "Academic Press Inc.",
number = "C",

}

TY - JOUR

T1 - Glycosyl phosphites as glycosylation reagents

AU - Aoki, Shin

AU - Kondo, Hirosato

AU - Wong, Chi Huey

PY - 1994/1/1

Y1 - 1994/1/1

N2 - This chapter describes the application of glycosyl phosphites to the synthesis of different types of glycosides. The development of new methods for the efficient construction of glycosidic bonds is an objective of current research in carbohydrate synthesis. The practical and stereo controlled synthesis of oligosaccharides containing sialic acid, for example, remains of particular interest because of their important roles in biological recognition and cellular communication. However, the steric hindrance of the anomeric center and the ease of elimination during activation and glycosylation make the sialylation reaction particularly difficult to execute in a high-yield and stereoselective manner. A novel and high-yield sialylation using sialyl phosphite as donor and trimethylsilyltrifluoromethane sulfonate (TMSOTf) as catalyst has been illustrated in the chapter.

AB - This chapter describes the application of glycosyl phosphites to the synthesis of different types of glycosides. The development of new methods for the efficient construction of glycosidic bonds is an objective of current research in carbohydrate synthesis. The practical and stereo controlled synthesis of oligosaccharides containing sialic acid, for example, remains of particular interest because of their important roles in biological recognition and cellular communication. However, the steric hindrance of the anomeric center and the ease of elimination during activation and glycosylation make the sialylation reaction particularly difficult to execute in a high-yield and stereoselective manner. A novel and high-yield sialylation using sialyl phosphite as donor and trimethylsilyltrifluoromethane sulfonate (TMSOTf) as catalyst has been illustrated in the chapter.

UR - http://www.scopus.com/inward/record.url?scp=0028673437&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028673437&partnerID=8YFLogxK

U2 - 10.1016/S0076-6879(94)47015-4

DO - 10.1016/S0076-6879(94)47015-4

M3 - Article

C2 - 7898353

AN - SCOPUS:0028673437

VL - 247

SP - 193

EP - 211

JO - Methods in Enzymology

JF - Methods in Enzymology

SN - 0076-6879

IS - C

ER -