β-l-Rhamnosylation and β-d-Mannosylation Mediated by 4-O-Ester Groups in a Weakly Nucleophilic Environment

Yongliang Zhang; Changsheng Chen; Yongtao Gao; Min Yang; Zehuan He; Bangzhi Zhang; Guofeng Gu; Bencan Tang; Feng Cai

doi:10.1021/acs.orglett.3c02566

β-l-Rhamnosylation and β-d-Mannosylation Mediated by 4-O-Ester Groups in a Weakly Nucleophilic Environment

Yongliang Zhang, Changsheng Chen, Yongtao Gao, Min Yang, Zehuan He, Bangzhi Zhang, Guofeng Gu, Bencan Tang, Feng Cai

Department of Chemical and Environmental Engineering

Research output: Journal Publication › Article › peer-review

3 Citations (Scopus)

Abstract

eq-4-O-Acyl group directed β-rhamnosylation and β-mannosylation are achieved in a carborane or BARF anion formed weakly nucleophilic environment with the assistance of a 2,3-orthocarbonate group. The 4-O-acyl group plays a critical role in directing the β-selectivity, and the weakly coordinating anion is essential to amplify this direction. The orthocarbonate group could be readily removed with 1,3-propanediol in the presence of BF₃·Et₂O.

Original language	English
Pages (from-to)	7120-7125
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	39
DOIs	https://doi.org/10.1021/acs.orglett.3c02566
Publication status	Published - 6 Oct 2023

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "β-l-Rhamnosylation and β-d-Mannosylation Mediated by 4-O-Ester Groups in a Weakly Nucleophilic Environment",

abstract = "eq-4-O-Acyl group directed β-rhamnosylation and β-mannosylation are achieved in a carborane or BARF anion formed weakly nucleophilic environment with the assistance of a 2,3-orthocarbonate group. The 4-O-acyl group plays a critical role in directing the β-selectivity, and the weakly coordinating anion is essential to amplify this direction. The orthocarbonate group could be readily removed with 1,3-propanediol in the presence of BF3·Et2O.",

author = "Yongliang Zhang and Changsheng Chen and Yongtao Gao and Min Yang and Zehuan He and Bangzhi Zhang and Guofeng Gu and Bencan Tang and Feng Cai",

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T1 - β-l-Rhamnosylation and β-d-Mannosylation Mediated by 4-O-Ester Groups in a Weakly Nucleophilic Environment

AU - Zhang, Yongliang

AU - Chen, Changsheng

AU - Gao, Yongtao

AU - Yang, Min

AU - He, Zehuan

AU - Zhang, Bangzhi

AU - Gu, Guofeng

AU - Tang, Bencan

AU - Cai, Feng

PY - 2023/10/6

Y1 - 2023/10/6

N2 - eq-4-O-Acyl group directed β-rhamnosylation and β-mannosylation are achieved in a carborane or BARF anion formed weakly nucleophilic environment with the assistance of a 2,3-orthocarbonate group. The 4-O-acyl group plays a critical role in directing the β-selectivity, and the weakly coordinating anion is essential to amplify this direction. The orthocarbonate group could be readily removed with 1,3-propanediol in the presence of BF3·Et2O.

AB - eq-4-O-Acyl group directed β-rhamnosylation and β-mannosylation are achieved in a carborane or BARF anion formed weakly nucleophilic environment with the assistance of a 2,3-orthocarbonate group. The 4-O-acyl group plays a critical role in directing the β-selectivity, and the weakly coordinating anion is essential to amplify this direction. The orthocarbonate group could be readily removed with 1,3-propanediol in the presence of BF3·Et2O.

UR - http://www.scopus.com/inward/record.url?scp=85175145049&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.3c02566

DO - 10.1021/acs.orglett.3c02566

M3 - Article

AN - SCOPUS:85175145049

SN - 1523-7060

VL - 25

SP - 7120

EP - 7125

JO - Organic Letters

JF - Organic Letters

IS - 39

ER -

β-l-Rhamnosylation and β-d-Mannosylation Mediated by 4-O-Ester Groups in a Weakly Nucleophilic Environment

Abstract

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