(3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester

Base Information

Chemical Name:(3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester
CAS No.:189328-22-1
Molecular Formula:C₃₈H₅₀O₅SSi
Molecular Weight:646.963
Hs Code.:

Synonyms:(3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester

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Chemical Property of (3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester

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Technology Process of (3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester

There total 5 articles about (3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 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: 94.0%

: 999-90-6
S-tert-butyl thioacetate

: 189328-21-0
(4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one

: 189328-22-1
(3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(97)00380-8

Reference yield:

: 171622-74-5
(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol

: 189328-22-1
(3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) DMSO (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) warm to room temperature

2: 80 percent / n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

3: 1.) DMSO (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) warm to room temperature

4: 94 percent / LHMDS / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 30 min

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane;
DOI:10.1021/jo9711089

Reference yield:

: 197219-76-4
(4R,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol

: 189328-22-1
(3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) DMSO (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) warm to room temperature

2: 94 percent / LHMDS / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 30 min

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1021/jo9711089