442631-65-4

Upstream product

• 335197-11-0 4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester 
• 442631-63-2 (3S,8R,9S,10R,13S,14S,16S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-{(R)-1-[2-(3-methyl-butyl)-[1,3]dioxolan-2-yl]-ethyl}-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-16,17-diol 
• 3068-31-3 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-L-arabinopyranose 
• 335197-14-3 (4-methyl-pent-1-ynyloxy)-cyclohexane 
• 335197-16-5 ((E)-1-Bromo-4-methyl-pent-1-enyloxy)-cyclohexane 
• 335197-22-3 (S)-1,2-O-(1-ethylthioethylidene)-α-D-xylopyranose 
• 332888-23-0 Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(R)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester 
• 442631-59-6 Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-{(R)-1-[2-(3-methyl-butyl)-[1,3]dioxolan-2-yl]-ethyl}-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester 
• 442631-61-0 (3S,8R,9S,10R,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-hydroxy-10,13-dimethyl-17-{(R)-1-[2-(3-methyl-butyl)-[1,3]dioxolan-2-yl]-ethyl}-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one 
• 442631-19-8 (3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-eth-(Z)-ylidene-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one 
• 335197-28-9 4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-phenylsulfanyl-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester 
• 335197-27-8 4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 
• 335197-26-7 4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Total synthesis of the anticancer natural product OSW-1

The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3β-ol-17-one 79 in 10 operations with 28% overall yield. The key steps in the total synthesis included a highly regio- and stereoselective selenium dioxide-mediated allylic oxidation of 80 and a highly stereoselective 1,4-addition of α-alkoxy vinyl cuprates 68 to steroid 17(20)-en-16-one 12E to introduce the steroid side chain. This total synthesis demonstrated once again the versatile synthetic applications of α-halo vinyl ether chemistry developed in our laboratories.