(3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

Base Information

Chemical Name:(3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one
CAS No.:1403584-96-2
Molecular Formula:C₂₅H₃₅NO₅S₂
Molecular Weight:493.689
Hs Code.:

Synonyms:(3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

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Chemical Property of (3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

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Technology Process of (3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

There total 8 articles about (3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1403584-89-3
3-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)propanal

: 255828-89-8
(S)-1-(4-(tert-butyl)-2-thioxothiazolidin-3-yl)ethan-1-one

: 1403584-96-2
(3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

: 1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

Guidance literature:: (S)-1-(4-(tert-butyl)-2-thioxothiazolidin-3-yl)ethan-1-one; With phenylborondichloride; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

With (-)-sparteine; In dichloromethane; at 20 ℃; for 0.5h;

3-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)propanal; In dichloromethane; at -78 - 0 ℃; for 4.25h; Overall yield = 85 percent; Overall yield = 16.7 g;

Reference yield:

: 1403584-89-3
3-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)propanal

: 255828-89-8
(S)-1-(4-(tert-butyl)-2-thioxothiazolidin-3-yl)ethan-1-one

: 1403584-96-2
(3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

Guidance literature:: (S)-1-(4-(tert-butyl)-2-thioxothiazolidin-3-yl)ethan-1-one; With phenylborondichloride; In dichloromethane; for 0.166667h; Inert atmosphere;

With (-)-sparteine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

3-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)propanal; In dichloromethane; at -78 - 20 ℃; for 7h; Inert atmosphere;
DOI:10.1021/ol3023006

Reference yield:

: 3-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)propan-1-ol

: 1403584-96-2
(3R)-1-((S)-4-(tert-butyl)-2-thioxothiazolidin-3-yl)-3-hydroxy-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: phenylborondichloride / dichloromethane / 0.17 h / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 7 h / -78 - 20 °C / Inert atmosphere

With phenylborondichloride; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane;
DOI:10.1021/ol3023006