Silyl-protective groups influencing the reactivity and selectivity in glycosylations

Mikael Bols; Christian Marcus Pedersen

doi:10.3762/bjoc.13.12

Silyl-protective groups influencing the reactivity and selectivity in glycosylations

Mikael Bols, Christian Marcus Pedersen

Department of Chemistry

35 Citations (Scopus)

155 Downloads (Pure)

Abstract

Silyl groups such as TBDPS, TBDMS, TIPS or TMS are well-known and widely used alcohol protective groups in organic chemistry. Cyclic silylene protective groups are also becoming increasingly popular. In carbohydrate chemistry silyl protective groups have frequently been used primarily as an orthogonal protective group to the more commonly used acyl and benzyl protective groups. However, silyl protective groups have significantly different electronic and steric requirements than acyl and alkyl protective groups, which particularly becomes important when two or more neighboring alcohols are silyl protected. Within the last decade polysilylated glycosyl donors have been found to have unusual properties such as high (or low) reactivity or high stereoselectivity. This mini review will summarize these findings

Original language	English
Journal	Beilstein Journal of Organic Chemistry
Volume	13
Pages (from-to)	93-105
Number of pages	13
ISSN	2195-951X
DOIs	https://doi.org/10.3762/bjoc.13.12
Publication status	Published - 16 Jan 2017

Keywords

Carbohydrate
conformation
glycosylation
reactivity
selectivity

Access to Document

10.3762/bjoc.13.12Licence: Other

Silyl-protective groups influencing the reactivity andFinal published version, 814 KBLicence: Other

Cite this

@article{7b24b5a74e76478bb44e1db0f94f9bac,

title = "Silyl-protective groups influencing the reactivity and selectivity in glycosylations",

abstract = "Silyl groups such as TBDPS, TBDMS, TIPS or TMS are well-known and widely used alcohol protective groups in organic chemistry. Cyclic silylene protective groups are also becoming increasingly popular. In carbohydrate chemistry silyl protective groups have frequently been used primarily as an orthogonal protective group to the more commonly used acyl and benzyl protective groups. However, silyl protective groups have significantly different electronic and steric requirements than acyl and alkyl protective groups, which particularly becomes important when two or more neighboring alcohols are silyl protected. Within the last decade polysilylated glycosyl donors have been found to have unusual properties such as high (or low) reactivity or high stereoselectivity. This mini review will summarize these findings",

keywords = "Carbohydrate, conformation, glycosylation, reactivity, selectivity",

author = "Mikael Bols and Pedersen, {Christian Marcus}",

year = "2017",

month = jan,

day = "16",

doi = "10.3762/bjoc.13.12",

language = "English",

volume = "13",

pages = "93--105",

journal = "Beilstein Journal of Organic Chemistry",

issn = "2195-951X",

publisher = "Beilstein - Institut zur Foerderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Silyl-protective groups influencing the reactivity and selectivity in glycosylations

AU - Bols, Mikael

AU - Pedersen, Christian Marcus

PY - 2017/1/16

Y1 - 2017/1/16

N2 - Silyl groups such as TBDPS, TBDMS, TIPS or TMS are well-known and widely used alcohol protective groups in organic chemistry. Cyclic silylene protective groups are also becoming increasingly popular. In carbohydrate chemistry silyl protective groups have frequently been used primarily as an orthogonal protective group to the more commonly used acyl and benzyl protective groups. However, silyl protective groups have significantly different electronic and steric requirements than acyl and alkyl protective groups, which particularly becomes important when two or more neighboring alcohols are silyl protected. Within the last decade polysilylated glycosyl donors have been found to have unusual properties such as high (or low) reactivity or high stereoselectivity. This mini review will summarize these findings

AB - Silyl groups such as TBDPS, TBDMS, TIPS or TMS are well-known and widely used alcohol protective groups in organic chemistry. Cyclic silylene protective groups are also becoming increasingly popular. In carbohydrate chemistry silyl protective groups have frequently been used primarily as an orthogonal protective group to the more commonly used acyl and benzyl protective groups. However, silyl protective groups have significantly different electronic and steric requirements than acyl and alkyl protective groups, which particularly becomes important when two or more neighboring alcohols are silyl protected. Within the last decade polysilylated glycosyl donors have been found to have unusual properties such as high (or low) reactivity or high stereoselectivity. This mini review will summarize these findings

KW - Carbohydrate

KW - conformation

KW - glycosylation

KW - reactivity

KW - selectivity

U2 - 10.3762/bjoc.13.12

DO - 10.3762/bjoc.13.12

M3 - Journal article

C2 - 28228850

SN - 2195-951X

VL - 13

SP - 93

EP - 105

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -