Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

Duc Thinh Khong; Zaher M.A. Judeh

doi:10.1016/j.tetlet.2016.11.116

Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

Duc Thinh Khong, Zaher M.A. Judeh^*

^*Corresponding author for this work

Nanyang Technological University

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

18 Citations (Scopus)

Abstract

A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me₂SnCl₂-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at O-6.

Original language	English
Pages (from-to)	109-111
Number of pages	3
Journal	Tetrahedron Letters
Volume	58
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2016.11.116
Publication status	Published - 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Elsevier Ltd

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Calceolarioside-B
Dimethyltin dichloride
Eutigoside-A
Phenylpropanoid glycosides
Regioselective acylation

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10.1016/j.tetlet.2016.11.116

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title = "Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A",

abstract = "A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at O-6.",

keywords = "Calceolarioside-B, Dimethyltin dichloride, Eutigoside-A, Phenylpropanoid glycosides, Regioselective acylation",

author = "Khong, {Duc Thinh} and Judeh, {Zaher M.A.}",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tetlet.2016.11.116",

language = "English",

volume = "58",

pages = "109--111",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

AU - Khong, Duc Thinh

AU - Judeh, Zaher M.A.

PY - 2017

Y1 - 2017

N2 - A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at O-6.

AB - A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at O-6.

KW - Calceolarioside-B

KW - Dimethyltin dichloride

KW - Eutigoside-A

KW - Phenylpropanoid glycosides

KW - Regioselective acylation

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DO - 10.1016/j.tetlet.2016.11.116

M3 - Article

AN - SCOPUS:85006277026

SN - 0040-4039

VL - 58

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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