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Synthesis, crystal structure, and conformation of methyl 6-deoxy-2,3-O-isopropylidene-α-d-manno-heptofuranoside

✍ Scribed by Janusz W. Krajewski; Przemysa̵w Gluziński; Zbigniew Pakulski; Aleksander Zamojski; Anatolii Mishnev; Andrejs Kemme

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
531 KB
Volume
252
Category
Article
ISSN
0008-6215

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✦ Synopsis

Methyl 6-deoxy-2,3-0-isopropylidene-a-D-manno-heptofuranoside (9) has been synthesised from the acetyliron complex 2 by a sequence of reactions involving deprotonation of 2, its reaction with aldehyde 5, decomplexation, isolation of 7, and reduction to 9. Compound 9 crystallises in the orthorbombic system, space group P2,2,2,, with cell dimensions: a = 6.097(l), b = 7.942(l), c = 26.862(3) A. The intensity data were collected with a Syntex P2, diffractometer. The structure was solved by direct methods and refined by the full-matrix, least-squares procedure, resulting in R = 0.049. The furanoside and 2,3-0-isopropylidene rings are characterised by envelope conformations 5_!? and E,, respectively. Relatively strong intermolecular hydrogen bonds were observed in the crystal structure.

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