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ChemInform Abstract: Convenient Synthesis of S- and Se-(2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl)-phosphorothioate, Phosphoroselenoate and Phosphorodithioate.

โœ Scribed by W. KUDELSKA

Publisher
John Wiley and Sons
Year
2010
Weight
42 KB
Volume
29
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Convenient Synthesis of S-and Se-(2,3,4,6-Tetra-O-benzyl-Dglucopyranosyl)-phosphorothioate, Phosphoroselenoate and Phosphorodithioate.

-BF 3 -mediated reaction of both 1-O-unprotected and 1-O-acyl sugars (I) with phosphorothioate (II), -selenate (IV) or -dithiolate (VI) provides the corresponding glucosyl phosphoroethers with ฮฑ-D-configuration. However, ฮฑ-glucosyl halides (VIII) react with phosphorodithioate (VI) in the presence of Et 3 N to furnish ฮฒ-D-configurated glucosyl phosphorodithioate (IX).

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ChemInform Abstract: Synthesis and Struc
ChemInform Abstract: Synthesis and Structural Studies of Anomeric 2,3,4,6-Tetra-O-acetyl-5-thio-D-glucopyranosyl Azides.
โœ Marianna Katona Strumpel; Juergen Buschmann; Laszlo Szilagyi; Zoltan Gyoergydeak ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 32 KB ๐Ÿ‘ 1 views

Synthesis and Structural Studies of Anomeric 2,3,4,6-Tetra-O-acetyl-5-thio-D-glucopyranosyl Azides. -Two alternative routes for the synthesis of both anomers of the title compound (II)/(III) are given. Both methods are comparable in yield but the route starting from glucopyranosyl bromide (I) is pr