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 mi
Tartraldehydes I. Synthesis of N-acetyl-D- and L-daunosamine and their xylo isomers
✍ Scribed by Pál Herczegh; Martina Zsély; Imre Kovács; Gyula Batta; Ferenc J Sztaricskai
- Book ID
- 104222032
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 202 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The title compounds were prepared from tartraldehyde dithioacetals' 1. and 2 using Wittig chain elongation, amino functionalization of the double bond and removal of the protective groups.
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N-Acyl derivatives of D,L-acosamine and D,L-ristosamine were synthesized with high stereoselectivity utilizing -7 -intramolecular Michael addition of Y-and 6-carbamoyloxy-a, P-unsaturated esters. Recently we have found prominent 1,2-and 1,3-asymmetric induction in the intramolecular Michael
I-0-Acyl derivatives of N-acetylmuramoyl-I.-alanyl-n-isogtutaminc (MDP) have been synthesized from 2-acctamido-l-O-bcnzoyl-4.6-O-isopropylidenc-3-0-[D-I-(methoxycarbonyI)ethyl]-e-D-glucopyranose. Their immunoadjuvant activities were examined in guinea-pigs. (N-ACETYL-I -0-ACYLMURAMOYI.).L-AI.ANYI.-
Title compound 1 was synthesized by a published route which had to be modified (seven steps from readily obtainable starting materials). Characterization of 1 was achieved by spectroscopic means (FAB-MS, ' H-NMR, including 2D-COSY). Furthermore, commercially available reference material purchased fo