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- W2000335178 abstract "A simple and efficient route to N-trifluoroacetyl-l-acosamine (13), N-trifluoroacetyl-l-daunosamine (12), and their 1-thio analogues (18 and 20) is described. Stereoselective reduction of oxime 5 with borane, followed by trifluoroacetylation resulted in the arabino methyl glycoside (8), which, on mild acid hydrolysis gave N-trifluoroacetyl-l-acosamine (13) in an overall yield of 33%, based on l-rhamnal (1). Upon oxidation of the C-4 hydroxyl group and stereoselective reduction of the resulting ketone 11, compound 8 of l-arabino configuration was converted into N-trifluoroacetyl-l-daunosamine (12) in a one-flask sequence with an overall yield of 28% calculated for 1. Benzyl 1-thio-N-trifluoroacetyl-α-l-acosaminide (18) was synthesized from enone 2 on Michael-type addition of phenylmethanethiol, followed by oximation, stereoselective reduction with borane and subsequent trifluoroacetylation. 4-O-Acetyl-1-S-acetyl-N-trifluoroacetyl-1-thio-β-l-daunosamine 20 was prepared from 12via the corresponding glycosyl chloride derivative." @default.
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- W2000335178 date "1986-02-01" @default.
- W2000335178 modified "2023-09-23" @default.
- W2000335178 title "Synthesis of N-trifluoroacetyl-l-acosamine, N-trifluoroacetyl-l-daunosamine, and their 1-thio analogs" @default.
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- W2000335178 doi "https://doi.org/10.1016/0008-6215(86)85039-x" @default.
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