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Syntheses of model oligosaccharides of biological significance. 8. A synthesis of a specifically deuterated 2-propyl 3,6-DI-O-[α-D-mannopyranosyl]-β-D-mannopyranoside

✍ Scribed by David S. Dime; Eliezer Rachaman; Charles E. Dime; Arthur A. Grey; Jeremy P. Carver; Jiri J. Krepinsky


Publisher
John Wiley and Sons
Year
1987
Tongue
French
Weight
446 KB
Volume
24
Category
Article
ISSN
0022-2135

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✦ Synopsis


The t i t l e trisaccharide has been synthesized containing a 3-deuterated central mannopyranosyl unit and 2,3,4,6,6'-pentadeuterio mannopyranosyl units i n both arms. 2-Propyl 2-0-benzyl-4,6-0-benzylidene-3-deuterlo- -I)-D-mannopyranoside was obtained by stereoselective deuteride reduction of the corresponding 3-0x0 derivative and was reacted with 2,3,4,6,6'-pentadeuterio-oc-D-mannopyranosyl bromide. The disaccharide obtained was glycosylated with another equivalent of the same bromide after hydrolysis of the benzylidene group.


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Syntheses of deoxy analogues of methyl 3
✍ Stefan Oscarson; Ulf Tedebark 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 920 KB

All of the monodeoxy analogues of methyl 3,6-di-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside have been synthesized together with two dideoxy (2,3'- and 4,3'-) analogues. The 2'- and 2"-deoxy functions were introduced by NIS-promoted couplings with 2,3,4-tri-O-acetyl-D-glucal as donor, followed b