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Enantiospecific synthesis of L-(3R; and 3S)-(β-D-ribofuranosyl)-pyroglutamic acids: Possible intermediates in C-nucleoside biosynthesis

✍ Scribed by Jack E. Baldwin; Robert M. Adlington; Nicholas G. Robinson


Book ID
104216379
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
231 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis


The stereospecific addition of a glycine anion equivalent to a P-ribosyl acrylate is the key step in the enantiospecific synthesis of L-3-(P-&ibofuranosyl)-pyroglutamic acids, possible intermediates in C-nucleoside biosynthesis.


📜 SIMILAR VOLUMES


Synthesis of [R-(R∗,S∗)]- and [S-(R∗,R∗)
✍ Taisuke Itaya; Tae Kanai; Takehiko Iida 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 213 KB

The synthesis of the title compounds started with the Vilsmeier reaction of 3-[2,3,5-tris-O-(tert-butylalmethylsilyl)-~-D-ribofuranosyl]wye (b'b) and proceeded through the Wittig reaction with (R)-N-(methoxyearbonyl)-3-(triphenylphosphonio)alaninate (4), methylation with trimethyisilyldiazomethane,