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Synthesis of Δ 20-Ginsenosides Rh 4, (20E)-Rh 3, Rg 6, and Rk 1: A General Approach To Access Dehydrated Ginsenosides

Synthesis of Δ 20-Ginsenosides Rh 4, (20E)-Rh 3, Rg 6, and Rk 1: A General Approach To Access Dehydrated Ginsenosides

Renzeng Shen, Stephane Laval, Xin Cao, Biao Yu

J Org Chem. 2018 Mar 2;83(5):2601-2610.

PMID: 29431441

Abstract:

Four representative Δ20-ginsenosides, namely, ginsenosides Rh4 (1), (20E)-Rh3 (2), Rg6 (3), and Rk1 (4) from Panax Ginseng, were chemically synthesized for the first time. Dehydration of the naturally occurring 20(S)-protopanaxatriol and 20(S)-protopanaxadiol provided all types of Δ20-sapogenins, which were separated due to a judicious choice of protecting groups. The Δ20-sapogenins were then directly glycosylated with glycosyl ortho-alkynylbenzoate donors under the catalysis of Ph3PAuNTf2 as key steps. The neutral conditions of the glycosylations were crucial to prevent the acid-labile Δ20,21 double bond from isomerization.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42410391	Pregnanediol-2,3,4,20,21-13C5			Price

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