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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Bibliographic Details
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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Summary: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.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.200990330