503314-24-7

Basic information

• Product Name: diosgenyl 3,6-di-O-benzyl-2,4-di-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside
• Synonyms: diosgenyl 3,6-di-O-benzyl-2,4-di-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside
• CAS NO: 503314-24-7
• Molecular Weight: 1590.05
• Mol File: 503314-24-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: diosgenyl 3,6-di-O-benzyl-2,4-di-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: diosgenyl 3,6-di-O-benzyl-2,4-di-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside(503314-24-7)
• EPA Substance Registry System: diosgenyl 3,6-di-O-benzyl-2,4-di-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside(503314-24-7)

Safety Data

• Hazardous Substances Data: 503314-24-7(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 60478-68-4 dioscin 
• 128962-63-0 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside 

Downstream Products

• 60478-68-4 dioscin 

Relevant articles and documents

A facile approach to diosgenin and furostan type saponins bearing a 3β-chacotriose moiety

Combination of a one-pot coupling technique and the use of benzyl ethers as permanent protecting groups offered a short and simple route to dioscin-type saponins. This strategy in combination with a mild reductive opening procedure of the spiroketal function in diosgenin also offered a convenient approach to bidesmosidic furostan type saponins. Me3N·BH3/AlCl3 promoted acetal opening of 3-O-TBDMS-protected diosgenin gave the 26-OH acceptor 9 into which a benzylated β-glucose moiety was introduced by a SN2-type imidate coupling. After cleavage of the silyl ether, the 3β-O-glucose and the 4-O-linked rhamnose of the chacotriose unit were introduced by a NIS/AgOTf-promoted one-pot coupling sequence utilising thioglycoside donors and their different reactivity in different solvents. After removal of a benzoyl group, the same coupling conditions were also used for the coupling of the second 2-O-linked rhamnose unit. The target substance was obtained after cleavage of the protecting benzyl ethers under Birch-type conditions, which did not affect the double bond in the steroid skeleton.