CONVERSION OF D-MANNOSE INTO 1,5-ANHYDRO-D-ALLITOL-4,6-ACETONIDE; UNUSUAL INTRAMOLECULAR EPOXY ALCOHOL OPENING IN BASE

DOI: 10.1016/0040-4039(91)80760-4

Source and publish data:

Tetrahedron Letters p. 6089 - 6092 (1991)

Update date:2022-09-26

Topics:

Authors:

Jung, Michael E.

Clevenger, Gary L.

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Article abstract of DOI:10.1016/0040-4039(91)80760-4

Treatment of 3-tosyl-D-mannose-4,6-acetonide 9 with sodium borohydride affords an epoxy alcohol 11 which on treatment with base gives 1,5-anhydro-D-allitol-4,6-acetonide 15 by a 6-endo opening of the rearranged epoxy alcohol 13 rather than the product of

Full text of DOI:10.1016/0040-4039(91)80760-4

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