Silyl-protective groups influencing the reactivity and selectivity in glycosylations
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Silyl-protective groups influencing the reactivity and selectivity in glycosylations. / Bols, Mikael; Pedersen, Christian Marcus.
In: Beilstein Journal of Organic Chemistry, Vol. 13, 2017, p. 93-105.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Silyl-protective groups influencing the reactivity and selectivity in glycosylations
AU - Bols, Mikael
AU - Pedersen, Christian Marcus
PY - 2017
Y1 - 2017
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
VL - 13
SP - 93
EP - 105
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 2195-951X
ER -
ID: 176370769