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The synthesis of 3-deoxy-L-fucose (3,6-dideoxy-L-xylo-hexose)

✍ Scribed by Lindhorst, Thisbe K. ;Thiem, Joachim

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
572 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The synthesis of 3‐deoxy‐L‐fucose (19) could not be achieved by an inversion procedure, starting from the 3‐O‐triflate‐activated derivatives 8 or 9, respectively. Also the Mitsunobu reaction with the 3‐OH‐unblocked sugars 6 or 7 did not lead to the desired compounds. Instead, the formation of the unexpected side products 10, 11 and 12 was observed and interpreted. However, an equilibrium mixture of 3‐deoxy‐L‐fucose 19 and 21 was successfully synthesized by utilizing a Barton‐type deoxygenation of methyl 2,4‐di‐O‐benzoyl‐α‐L‐fucoside (7). The latter compound could be obtained from methyl α‐L‐fucoside (1) in a one‐pot reaction and crystallization in approximately 70% yield.

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