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Hydroformylation of cyclopentenes, novel strategy for total synthesis of carba-d-fructofuranose

โœ Scribed by Mohindra Seepersaud; Mika Kettunen; Adnan S Abu-Surrah; Timo Repo; Wolfgang Voelter; Yousef Al-Abed

Book ID
104250578
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
147 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Carba-D-fructofuranose (2a) was synthesized in 3 steps from cyclopentene 3. Compound 3 was prepared in 90% yield from commercially available 2,3,5-tri-O-benzyl-D-arabinose. The C-5 hydroxylmethyl unit was incorporated into 3 via hydroformylation using Wilkinson's catalyst. Reduction and hydrogenation afforded carba-D-fructofuranose (2a).

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