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Contribution of the O-benzoyl groups of tetra-O-benzoyl-α,β-l-arabinopyranoses to the formation of 1,1-bis(benzamido)-1-deoxy-l-arabinitol

✍ Scribed by Silvia R. Leicach; Raúl A. Cadenas; Jorge F. Sproviero

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 399 KB
Volume: 240
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84173-4

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✦ Synopsis

Several 1,2,3,4-tetra-0-benzoyl-I_-arabinopyranoses selectively labeled with C,Hs['4C]C0 groups at different positions were synthesized. Their reactions with methanolic ammonia afforded a labeled l,l-bis(benzamido)-1-deoxy-L-arabinitol (18). The contribution of each benzoyl group to the formation of the two benzamido linkages in 18 was ascertained by activity measurements.

C,H,CO-2 made the smallest contribution to the formation of 18, whereas those at O-3 and O-4 made the greatest contribution.

C,H,CO-1 did not contribute to the migration reaction.

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