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Synthesis of substituted 2,6-dioxabicyclo[3.1.1]heptanes:1,3-anhydro-2,4-di-O-benzyl-6-deoxy-β-l-talopyranose

✍ Scribed by Zhonghong Gan; Fanzuo Kong

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
281 KB
Volume
270
Category
Article
ISSN
0008-6215

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✦ Synopsis

Removal of the isopropylidene group under mild acidic conditions gave methyl 4-O-benzyl-6-deoxy-a-L-talopyranoside (3). Treatment of the dibutylstannylene derivative of compound 3 with benzyl bromide (2 equiv) and tetrabutylammonium bromide (1 equiv) in toluene afforded the 2-O-benzyl derivative 4 in 30% yield, together with methyl 3,4-di-O-benzyl-6-deoxy-a-L-talopyranoside (9). Aspinall and Takeo [14] reported a similar method for the preparation of benzyl 2,4-di-O-* Corresponding author.

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