Synthesis of higher-carbon sugars: preparation and reaction of β-hydroxysulfonyl sugars
✍ Scribed by Kwan Soo Kim; Jae-Kyung Sohng; Sung Bum Ha; Chan Seong Cheong; Dai Il Jung; Chi Sun Hahn
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 204 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
The catalytic osmylation of the following higher-carbon sugar allylic alcohols and enones was examined.
Strictly speaking, these compounds are C,, sugar derivatives but, because of their resemblance to disaccharides and for easier comprehension. they are named as x-deoxy-x-(C-glycosyI)glycose derivatives.
3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-a-D-xylo-hexadialdo-1,4-furanose (2) upon treatment with Lirv(TMS)2 at -500 furnished the e&ate which reacted with methyl 2,3,4-tri-Obenzyl-a-D-glucopyranoside-6-ulose (5) to afford two eythro aldols 3 and 4 in 6:l ratio and 43% yield. 5R;6R Confguration was a
The Bu3SnH -AIBN induced radical additions of 3,5-di-g-acetyl-6deoxy-6-iodo-l,Z-O-isopropylidene-a-B\_gluco-and -allofuranose (I and lo), and methyl 5-deoxy-5-~odo-2,3-O-isopropylidene-8-B-ribofuranoside (19) to dimethyl maleate, methyl acrylate, acrylonitrile, methyl vinyl ketone, and vinylene carb
The Bu3SnH -AIBN induced radical cyclization of 6-bromo-b-deoxy-3-~-[(~)-2-ethoxycarbonylethenyll\_1,2-O\_is-allofuranose (1) gave ethyl 3,7-anhydro-6,8-dideoxy-l,2-O-isopropylidene-~-~-glycero-~-allo-nono--furanuronate (2) in 80% yield. Similar cvclizations of furanose derivatives and a synthesis.