A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4-SiO2

Hai Xia Liu; Qin Pei Wu; Yi Nan Shu; Xi Chen; Xiao Dong Xi; Ti Jian Du; Qing Shan Zhang

doi:10.1016/j.carres.2009.08.035

A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO₄-SiO₂

Hai Xia Liu, Qin Pei Wu^*, Yi Nan Shu, Xi Chen, Xiao Dong Xi, Ti Jian Du, Qing Shan Zhang

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

13 Citations (Scopus)

Abstract

The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO₄-SiO₂ under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl β-d-furanosides with a 2-acetoxyisopropyl group.

Original language	English
Pages (from-to)	2342-2348
Number of pages	7
Journal	Carbohydrate Research
Volume	344
Issue number	17
DOIs	https://doi.org/10.1016/j.carres.2009.08.035
Publication status	Published - 23 Nov 2009

Keywords

Acetals
Esterification
Esters
Heterogeneous catalysis
Protecting groups

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10.1016/j.carres.2009.08.035

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title = "A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4-SiO2",

abstract = "The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4-SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl β-d-furanosides with a 2-acetoxyisopropyl group.",

keywords = "Acetals, Esterification, Esters, Heterogeneous catalysis, Protecting groups",

author = "Liu, \{Hai Xia\} and Wu, \{Qin Pei\} and Shu, \{Yi Nan\} and Xi Chen and Xi, \{Xiao Dong\} and Du, \{Ti Jian\} and Zhang, \{Qing Shan\}",

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T1 - A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4-SiO2

AU - Liu, Hai Xia

AU - Wu, Qin Pei

AU - Shu, Yi Nan

AU - Chen, Xi

AU - Xi, Xiao Dong

AU - Du, Ti Jian

AU - Zhang, Qing Shan

PY - 2009/11/23

Y1 - 2009/11/23

N2 - The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4-SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl β-d-furanosides with a 2-acetoxyisopropyl group.

AB - The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4-SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl β-d-furanosides with a 2-acetoxyisopropyl group.

KW - Acetals

KW - Esterification

KW - Esters

KW - Heterogeneous catalysis

KW - Protecting groups

UR - http://www.scopus.com/inward/record.url?scp=70350502820&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2009.08.035

DO - 10.1016/j.carres.2009.08.035

M3 - Article

C2 - 19783241

AN - SCOPUS:70350502820

SN - 0008-6215

VL - 344

SP - 2342

EP - 2348

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 17

ER -

A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO₄-SiO₂

Abstract

Keywords

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