ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Insertion of the glycosylidene carbenes, derived from the gluco- and the manno-diazirines 1 and 2, into the Sn—H bond of R3SnH (R = Bu or Ph) leads to the fully substituted stannoglycosides 3-8 (53-77%). The 1,2-cis-configurated products are formed preferentially (α-D/β -D ranges from 2.5:1 to 5.1:1 with 1, and 1:1.3 to 1:4.2 with 2). Relative to CH2Cl2, THF favors formation of the equatorial Sn-glycosides. The stannylated (benzyloxy)glucals 9 and 10 were isolated as side products. The reaction of 1 with (Bu3Sn)2 yielded 9 (17% in CH2Cl2; 36% in CCl4) together with the azines 11 and the benzyloxyglucal 12. NMR Data of the Sn-glycosides 3-8 show evidence for an anomeric effect, 1J(C(1),H) being larger in the axial and 1J(Sn,C(1)) larger in the equatorial anomers.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19940770521
