637029-17-5

Basic information

• Product Name: (22R,25R)-3β-O-tert-butyldiphenylsilyloxy-26-hydroxy-5-furosten
• Synonyms: (22R,25R)-3β-O-tert-butyldiphenylsilyloxy-26-hydroxy-5-furosten
• CAS NO: 637029-17-5
• Molecular Weight: 655.049
• Mol File: 637029-17-5.mol

Chemical Properties

• CAS DataBase Reference: (22R,25R)-3β-O-tert-butyldiphenylsilyloxy-26-hydroxy-5-furosten(CAS DataBase Reference)
• NIST Chemistry Reference: (22R,25R)-3β-O-tert-butyldiphenylsilyloxy-26-hydroxy-5-furosten(637029-17-5)
• EPA Substance Registry System: (22R,25R)-3β-O-tert-butyldiphenylsilyloxy-26-hydroxy-5-furosten(637029-17-5)

Safety Data

• Hazardous Substances Data: 637029-17-5(Hazardous Substances Data)

Upstream product

• 324740-29-6 3-O-(tert-butyldiphenylsilyl)diosgenin 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 637029-18-6 (22R,25R)-3β-O-tert-butyldiphenylsilyloxy-26-p-methoxybenzyloxy-5-furosten 
• 637029-19-7 (22R,25R)-3β-hydroxy-26-p-methoxybenzyloxy-5-furosten 
• 637029-29-9 C₅₃H₉₀O₉Si₂ 
• 637029-28-8 (22R,25R)-3β-(2,4-di-O-benzoyl-3,6-di-O-tert-butyldimethylsilyl-β-D-glucopyranosyloxy)-26-p-methoxybenzyloxy-5-furosten 
• 14320-81-1 20-epi-verazine 

Relevant articles and documents

Stereoselective Synthesis of (-)-Verazine and Congeners via a Cascade Ring-Switching Process of Furostan-26-acid

An efficient synthetic strategy for three natural seco-type cholestane alkaloids isolated from the Veratrum plants, based on commercially available naturally occurring and abundant (-)-diosgenin (1), as exemplified in the concise asymmetric synthesis of (-)-verazine (4), (-)-veramiline (5) (proposed structure), and its 22-epimer, (-)-oblonginine (6), is presented. This work highlights the application of a cascade ring-switching process of (-)-diosgenin to achieve the E-ring opening and construction of chiral six-membered lactone challenges in seco-type cholestane alkaloid synthesis. This approach enables the synthesis of related natural and nature-like novel cholestane alkaloids, opening up opportunities for more extensive exploration of cholestane alkaloid biology.

Synthesis of Dihydrodiosgenin Glycosides as Mimetics of Bidesmosidic Steroidal Saponins

The focus of this work is the synthesis of bidesmosidic saponin mimetics. Therefore, dihydrodiosgenin derivatives, which differ from the natural compounds by reduction of the 22-(hemi) acetal were used as glycosyl acceptors. In preliminary studies, the dihydrodiosgenin glycosides 16, 17 and 19, as well as trisaccharide 22, were synthesized. The acceptors 10 and 14 were subjected to DMTST-mediated glucosylation for the synthesis of the chacotriose-substituted compound 3. For a selective 2,4-di-rhamnosylation of the dihydrodiosgenin glucopyranoside, differentiation of the glucose OH groups was achieved by selective benzoylation with 1-(benzoyloxy)benzotriazole. Reaction of the 3,6-di-O-benzoate 32 with the perbenzoylated ethyl thiorhamnopyranoside donor 15 gave the 2,4-di-rhamnosylated compound 33, together with the mono-rhamnosylated derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.