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

Base Information

• Chemical Name: (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one
• CAS No.: 189328-21-0
• Molecular Formula: C₃₂H₃₈O₄Si
• Molecular Weight: 514.737
• Mol file: 189328-21-0.mol

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

Chemical Property of (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one

There total 4 articles about (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-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: 90.0%

(4R,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol (197219-76-4) → (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one (189328-21-0)

Guidance literature:

Swern oxid.;

DOI:10.1016/S0040-4039(97)00380-8

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol (171622-74-5) → (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one (189328-21-0)

Guidance literature:

Multi-step reaction with 3 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

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane;

DOI:10.1021/jo9711089

Reference yield:

(2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal (162630-99-1) → (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one (189328-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

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

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane;

DOI:10.1021/jo9711089

upstream raw materials:

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

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

(2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal

phenylacetylene

Downstream raw materials:

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

3,4-bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one

[(2S,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester

(3S,4S,5R)-4,5-Bis-benzyloxy-3,6-dihydroxy-3-((Z)-styryl)-hexanethioic acid S-tert-butyl ester