A Vicinal Acyloxy Group Participation SN2 Reaction of Thiol Nucleophiles in the Formation of Thioacetals

Thioacetalization of acyl protected furanosides led to products with an ethanethiol group at C‐2 and 3‐O‐acetyl‐ 1,2‐di‐O‐isopropylidene‐D‐furanoses were converted into corresponding thioacetals with two ethanethiol groups at both C‐2 and C‐3 positions under the standard thioacetalization conditions...

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Published in:Chinese journal of chemistry 2009-10, Vol.27 (10), p.1962-1966
Main Authors: Wu, Qinpei, Xi, Xiaodong, Chen, Xi, Li, Hui, Zhang, Qingshan
Format: Article
Language:English
Subjects:
acetal
acyl group
protecting group
thioacetal
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container_end_page 1966
container_issue 10
container_start_page 1962
container_title Chinese journal of chemistry
container_volume 27
creator Wu, Qinpei
Xi, Xiaodong
Chen, Xi
Li, Hui
Zhang, Qingshan
description Thioacetalization of acyl protected furanosides led to products with an ethanethiol group at C‐2 and 3‐O‐acetyl‐ 1,2‐di‐O‐isopropylidene‐D‐furanoses were converted into corresponding thioacetals with two ethanethiol groups at both C‐2 and C‐3 positions under the standard thioacetalization conditions. All products were characterized by 1H NMR, 13C NMR and HRMS data. X‐ray structure analysis indicates that the vicinal acyloxy group is stereoselectively substituted by ethanethiols. The supposed mechanisms for these two kinds of transformations were presented. Thioacetalization of acyl protecting furanosides and 3‐O‐acetyl‐1,2‐di‐O‐isopropylidene‐D‐furanoses led to thioacetal products with an ethanethiol groups at C‐2 and two ethanethiol groups at both C‐2 and C‐3 positions, respecrively, under the standard thioacetalization conditions.
doi_str_mv 10.1002/cjoc.200990330
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All products were characterized by 1H NMR, 13C NMR and HRMS data. X‐ray structure analysis indicates that the vicinal acyloxy group is stereoselectively substituted by ethanethiols. The supposed mechanisms for these two kinds of transformations were presented. Thioacetalization of acyl protecting furanosides and 3‐O‐acetyl‐1,2‐di‐O‐isopropylidene‐D‐furanoses led to thioacetal products with an ethanethiol groups at C‐2 and two ethanethiol groups at both C‐2 and C‐3 positions, respecrively, under the standard thioacetalization conditions.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.200990330</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>acetal ; acyl group ; protecting group ; thioacetal</subject><ispartof>Chinese journal of chemistry, 2009-10, Vol.27 (10), p.1962-1966</ispartof><rights>Copyright © 2009 SIOC, CAS, Shanghai &amp; WILEY‐VCH Verlag GmbH &amp; Co. 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subjects acetal
acyl group
protecting group
thioacetal
title A Vicinal Acyloxy Group Participation SN2 Reaction of Thiol Nucleophiles in the Formation of Thioacetals
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