ISSN:
0947-3440
Keywords:
Sugars, branched-chain
;
α-Oxoketene dithioacetals
;
Pyrano[3,4-c]pyrazoles
;
Hydrodesulfurization, stereo-selective
;
Tributyltin hydride
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The stereoselective reduction of methyl 4,6-O-benzylidene-3-[bis(methylthio)methylene]-3-deoxy-α-D-erythro-hexopyranosid-2-ulose 1 with sodium tetrahydridoborate and tributyltin hydride, respectively, to (Z)-configured 4 is described. The increased reactivity of 4 compared to 1 is reflected in several substitution reactions resulting in the displacement of the methylthio group by different N nucleophiles. The substitution products 6-8 were stereoselectively obtained as (Z) isomers. Pyrano[3,4-c]pyrazole derivatives 3 and 10 were prepared by treatment of 1 and 4, respectively, with hydrazine hydrate.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199509226
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