THE NEW SYNTHESIS OF D-GLUCOSIDIC SPIROORTHOESTERS USING THE STEREOSELECTIVE PHOTOCYCLIZATION OF HYDROXYALKYL-D-GLUCOSIDES

被引:23
作者
PRALY, JP
DESCOTES, G
GRENIERLOUSTALOT, MF
METRAS, F
机构
[1] UNIV LYON 1, CNRS, ERA 689, ESCIL, CHIM ORGAN LAB 2, F-69622 VILLEURBANNE, FRANCE
[2] UNIV PAU & PAYS ADOUR, CNRS, ERA 895, CHIM ORGAN PHYS LAB, F-64000 PAU, FRANCE
关键词
D O I
10.1016/0008-6215(84)85081-8
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Irradiation of hydroxyalkyl glucosides in the presence of mercury(II) oxide and iodine gave glucosidic C-1-spiroorthoesters. Where the starting glycoside had CH2OH, the cyclization was regio- and stereo-specific by .alpha.-attack. The C-1-spiroorthoesters were readily available in a 1-pot synthesis starting from glucosyl halides. [Spiroorthoesters are found in some antibiotics].
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页码:21 / 35
页数:15
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