Total Asymmetric Synthesis of 5-Deoxy-5-thio- l -allose
β Scribed by Emery, Fabienne; Vogel, Pierre
- Book ID
- 121264590
- Publisher
- Taylor and Francis Group
- Year
- 1994
- Tongue
- English
- Weight
- 522 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0732-8303
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π SIMILAR VOLUMES
The syntheses have been described of the 2-acetamido-2-deoxy derivatives of 5-thio-D-glucose lm3, 5-thio-D-mannose 4, 5-thio-D-allose 5, 3-acetamido-3-deoxy5thio-D-xylose6, and 4-acetamido-4-deoxy-5-thio-r\_-lyxose6. We now report the syntheses of 3-amino-3-deoxy-5-thio-D-allose hydrochloride and a
ABSTRAm 5,6-Anhydro-1,2-0-isopropylidene-3-O-methanesulphonyl-a-~-idofuranose was converted, via the related gZucod$-episulphide, into 6-0-acetyl-5-S-acetyl-1,2-O-isopropylidene-3-O-methanesulphonyl-5-thio-at-D-glucofuranose (9). Replacement of the acetyl groups of 9, or the related 3-toluene-p-sulp
Three routes were investigated for the conversion of D-glucose into the title compound. In the first approach, reduction of the 5,6-thiirane ring of 5,6-dideoxy-5,6-epithio-1,2-O-isopropylidene-t~-D-glucofuranose (17) as well as that of its 3-O-allyl derivative (13) with lithium aluminium hydride wa