478287-10-4

Upstream product

• 387821-77-4 (20S)-6β-methoxy-16β,17α-dihydroxy-3α,5α-cyclo-23-norcholanaldehyde 23,16-hemiacetal 
• 321125-08-0 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate 
• 721958-88-9 C₂₃H₃₆O₄ 
• 285979-64-8 (20S)-6β-methoxy-17α-hydroxy-3α,5α-cyclopregnane-20,16β-carbolactone 

Downstream Products

• 478286-92-9 6β-methoxy-3α,5α-cyclocholestane-16β,17α,22-triol 16-O-{O-[3,4-di-O-triethylsilyl-2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-α-L-arabinopyranoside} 
• 145075-81-6 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside} 

Relevant academic research and scientific papers

Synthesis of analogues of a potent antitumor saponin OSW-1

A series of side chain analogues (5a-e), a 22-glycosylated isomer (10), and 16β-O-L-arabinosyl (13a) or 16β-O-D-xylosyl (13b) analogues of OSW-1 were synthesized. All analogues were found to be less cytotoxic against breast and endometrial cancer cell lines than the natural product.

Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity.

The potent antitumor agent OSW-1 was synthesized from the protected aglycone in different ways. It was proven that direct glycosylation of the aglycone in its hemiketal form could be achieved, affording the protected OSW-1 in a moderate yield. Alternatively, regioselective protection of the triol obtained by reduction of the aglycone, followed by glycosylation, deprotection and oxidation yielded the same OSW-1 derivative. The third approach to this compound consisted of glycosylation of the previously described lactol [Morzycki, J. W.; Gryszkiewicz, A. Polish J. Chem. 2001, 75, 983-989], reaction of the resulting aldehyde with a Grignard reagent, and oxidation. OSW-1 obtained on removal of the protective groups was identical with the natural product.