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Preparation of methyl 4,6-O-benzylidene-2-chloro- and -2-bromo-α- and β-d-xylo-hexopyranosid-3-uloses and their α-d-ribo isomers, and formation of glycosid-3-ulose hydrates for the β-d-xylo isomers
✍ Scribed by Tohru Sakakibara; Toshio Nakagawa
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- English
- Weight
- 772 KB
- Volume
- 191
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The title glycosid-Iuloses were prepared from 3-nitro-@-D-three-hex-2-enopyranoside derivatives. 'H-N.m.r. spectral studies revealed that the 2-bromo-and 2-chloro-P-D-xylo-hexopyranosid-3-uloses readily equilibrated with their hydrates, but the remaining glycosid-3-uloses, including the cy-D-xylo and (Y-and /3-D-ribo isomers, were not hydrated under similar conditions.
📜 SIMILAR VOLUMES
Both 'H-and 13C-n.m.r. spectroscopy have been employed in structural studies of the 4,6-O-benzylidene-D-aldohexopyranosides and derivatives, including some deoxy sugars . I4 We now report i3C-n.m.r. data (Table I) for the 4,6-O-benzylidene derivatives of methyl 2-deoxy-( 2) 2-deoxy-3-O-methyl-(3),
## Abstract 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
IZUMI TAKAI, YOSHIFUSA TACHIMORI, AZUMA YAMAMOTO, YOSHIHARU ISHIDO\*, AND (the late) ROKURO SUWH