The first synthesis of 7-(hydroxymethyl)thiepane-3,4,5-triols from d-(-)-quinic acid

Tzenge Lien Shih; Wei Lin Gao

doi:10.1016/j.tet.2012.12.047

The first synthesis of 7-(hydroxymethyl)thiepane-3,4,5-triols from d-(-)-quinic acid

Tzenge Lien Shih^*, Wei Lin Gao

^*Corresponding author for this work

Tamkang University

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

8 Scopus citations

Abstract

Seven thiepanes, the seven-membered-ring thiosugars, were first synthesized in 11-12 steps starting from d-(-)-quinic acid. Each thiepane is unique for its flexible conformation with a hydroxymethyl group at its C7 position. The key step was the deprotection of ether groups in compounds 7, 8, and 18-21 by 1.0 M BCl₃ of CH₂Cl₂ solution at -78 °C to lead to the corresponding thiepanes. These target molecules all exhibited the twisted chair conformation that fully agreed with our previous report.

Original language	English
Pages (from-to)	1897-1903
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	7
DOIs	https://doi.org/10.1016/j.tet.2012.12.047
State	Published - 18 02 2013
Externally published	Yes

Keywords

Glycosidase inhibitors
Thiepanes
Thiosugars
d-(-)-Quinic acid

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10.1016/j.tet.2012.12.047

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abstract = "Seven thiepanes, the seven-membered-ring thiosugars, were first synthesized in 11-12 steps starting from d-(-)-quinic acid. Each thiepane is unique for its flexible conformation with a hydroxymethyl group at its C7 position. The key step was the deprotection of ether groups in compounds 7, 8, and 18-21 by 1.0 M BCl3 of CH2Cl2 solution at -78 °C to lead to the corresponding thiepanes. These target molecules all exhibited the twisted chair conformation that fully agreed with our previous report.",

keywords = "Glycosidase inhibitors, Thiepanes, Thiosugars, d-(-)-Quinic acid",

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AU - Shih, Tzenge Lien

AU - Gao, Wei Lin

PY - 2013/2/18

Y1 - 2013/2/18

N2 - Seven thiepanes, the seven-membered-ring thiosugars, were first synthesized in 11-12 steps starting from d-(-)-quinic acid. Each thiepane is unique for its flexible conformation with a hydroxymethyl group at its C7 position. The key step was the deprotection of ether groups in compounds 7, 8, and 18-21 by 1.0 M BCl3 of CH2Cl2 solution at -78 °C to lead to the corresponding thiepanes. These target molecules all exhibited the twisted chair conformation that fully agreed with our previous report.

AB - Seven thiepanes, the seven-membered-ring thiosugars, were first synthesized in 11-12 steps starting from d-(-)-quinic acid. Each thiepane is unique for its flexible conformation with a hydroxymethyl group at its C7 position. The key step was the deprotection of ether groups in compounds 7, 8, and 18-21 by 1.0 M BCl3 of CH2Cl2 solution at -78 °C to lead to the corresponding thiepanes. These target molecules all exhibited the twisted chair conformation that fully agreed with our previous report.

KW - Glycosidase inhibitors

KW - Thiepanes

KW - Thiosugars

KW - d-(-)-Quinic acid

UR - http://www.scopus.com/inward/record.url?scp=84872799116&partnerID=8YFLogxK

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DO - 10.1016/j.tet.2012.12.047

M3 - 文章

AN - SCOPUS:84872799116

SN - 0040-4020

VL - 69

SP - 1897

EP - 1903

JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -

The first synthesis of 7-(hydroxymethyl)thiepane-3,4,5-triols from d-(-)-quinic acid

Abstract

Keywords

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