C-STANNYLATED CARBOHYDRATE-DERIVATIVES .5. 1,2-5,6-DI-O-ISOPROPYLIDENE-3-C-(ORGANOSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE AND 1,2-5,6-DI-O-ISOPROPYLIDENE-3-C-(PHENYLSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE COMPOUNDS - X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF 1,2-5,6-DI-O-ISOPROPYLIDENE-3-C-(TRIPHENYLSTANNYLMETHYL)-ALPHA-D-ALLOFURANOSE

被引：19
|
作者：
BURNETT, LA [1 ]
DOIDGEHARRISON, SMSV [1 ]
GARDEN, SJ [1 ]
HOWIE, RA [1 ]
TAYLOR, OJ [1 ]
WARDELL, JL [1 ]
机构：
[1] UNIV ABERDEEN,DEPT CHEM,MESTON WALK,ABERDEEN AB9 2UE,SCOTLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 14期
关键词：
D O I：
10.1039/p19930001621
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The crystal structure and the solid state (C-13 and Sn-119) and solution (H-1, C-13 and Sn-119) NMR spectra of 1,2:5,6-di-O-isopropylidene-3-C-triphenylstannylmethyl-alpha-D-allofuranose (1; R = Ph) have been obtained. The structure of compound (1; R = Ph) is similar in both phases and contains a slightly distorted tetrahedral tin atom (C-Sn-C valency angles range from 103.8(3) to 114.9(5)-degrees]. The beta-oxygen atom at C(3) in compound (1; R = Ph) is 3.01 (1) A distant from Sn and is ideally sited to take part in nucleophilic assistance during Ph-Sn bond-cleavage reactions. Reactions of compound (1; R = Ph) and 1,2:5,6-di-0-isopropylidene-3-C-R3Sn-alpha-D-allofuranose with electrophiles (e.g., I2 or CF3CO2H) are also reported.
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收藏
页码：1621 / 1628
页数：8
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