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Synthesis of Sphingosine Relatives, XVII! Synthesis of (2S,2' R,3R,3' E,4E,8E)-1-O-(β-D-Glucopyranosyl)-N-(2'-hydroxy-3'-octadecenoyl)-9-methyl-4,8-sphingadienine (Pen II), the Major Cerebroside Isolated from Penicillium funiculosum as the Fruiting-Induce

✍ Scribed by Mori, Kenji ;Uenishi, Keiji

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
586 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Pen II [(2__S__,2' R,3__R__,3' E,4__E__,8__E__)‐1‐O‐(β‐D‐glucopyranosyl)‐N‐(2'‐hydroxy‐3'‐octadecenoyl)‐9‐methyl‐4,8‐sphingadienine], the major component of the cerebrosides isolated from Penicillium funiculosum A‐1 as the fruiting inducer against Schizophyllum commune, was synthesized by starting from D‐glucose, L‐serine, (2__R__,3__E__)‐2‐(tert‐butyldiphenylsilyloxy)‐3‐octadecenoic acid, and (E)‐6‐methyl‐5‐pentadecen‐1‐yne.

📜 SIMILAR VOLUMES

Synthesis of sphingosine relatives, IX.
Synthesis of sphingosine relatives, IX. Synthesis of (2S,3R,4E)-1-O-(β-D-glucopyranosyl)-N- [24-(linoleoyloxy)tetracosanoyl]-4-sphingenine. The structure proposed for the esterified cerebroside in the epidermis of guinea pigs
✍ Mori, Kenji ;Nishio, Hiroyuki 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 504 KB

## Abstract (2S,3R,4E)‐1‐O‐(β‐D‐Glucopyranosyl)‐N‐[24‐(linoleoyloxy)tetracosanoyl)‐4‐sphingenine (1) was synthesized from D‐glucose (A), (2S,3R,4E)‐4‐sphingenine (sphingosine, B), 24‐hydroxytetracosanoic acid (C) and linoleic acid (D). The ^1^H‐NMR spectrum of synthetic 1 was different from that of