Total Synthesis of Carbohydrates: Stereoselective Syntheses of 2,6-Dideoxy-D-arabino-hexose and 2,6-Dideoxy-D-ribo-hexose

DOI: 10.1021/jo00346a050

Source and publish data:

Journal of Organic Chemistry p. 1371 - 1373 (1982)

Update date:2022-07-29

Topics:

Authors:

Roush, William R.

Brown, Richard J.

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Article abstract of DOI:10.1021/jo00346a050

Short, highly stereoselective syntheses of the title carbohydrates from allylic alcohol precursors are described.A synthesis of the racemic arabino-deoxyhexose is also described.These syntheses feature the highly regioselective epoxide ring opening reactions of intermediates 7, 11, and 12 and the asymmetric epoxidation-kinetic resolution of allylic alcohol 10.

Full text of DOI:10.1021/jo00346a050

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