2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester
• CAS No.: 214273-39-9
• Molecular Formula: C₂₆H₄₂O₄Si
• Molecular Weight: 446.703
• Mol file: 214273-39-9.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester

There total 5 articles about 2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl 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:

2,2-Dimethyl-propionic acid (1S,4S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-4-methyl-5-oxo-7-trimethylsilanyl-hept-6-ynyl ester (214273-38-8) → 2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester (214273-39-9) + 2,2-Dimethyl-propionic acid (1S,4S,5R)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester

Guidance literature:

With dimethylsulfide borane complex; chiral oxazaborolidine (S config.); In tetrahydrofuran; at 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(98)01420-8

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → 2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester (214273-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / TfOSiMe₃

2: 1.) TBAF / 1.) THF, rt.; 2.) Swern oxidn.

3: 1.) THF, -78 degC; 2.) Swern oxidn.

4: BH₃:SMe₂, chiral oxazaborolidine (S config.) / tetrahydrofuran / 0 °C

With trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; chiral oxazaborolidine (S config.); tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01420-8

Reference yield:

2,2-Dimethyl-propionic acid (1S,4S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-4-methyl-5-oxo-pentyl ester (214273-37-7) → 2,2-Dimethyl-propionic acid (1S,4S,5S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-hydroxy-4-methyl-7-trimethylsilanyl-hept-6-ynyl ester (214273-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) THF, -78 degC; 2.) Swern oxidn.

2: BH₃:SMe₂, chiral oxazaborolidine (S config.) / tetrahydrofuran / 0 °C

With dimethylsulfide borane complex; chiral oxazaborolidine (S config.); In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01420-8

upstream raw materials:

2,2-Dimethyl-propionic acid (1S,4S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-4-methyl-5-oxo-7-trimethylsilanyl-hept-6-ynyl ester

O-benzyl 2,2,2-trichloroacetimidate

2,2-Dimethyl-propionic acid (1S,4S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-4-methyl-5-oxo-pentyl ester

2,2-Dimethyl-propionic acid (1S,4S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-(tert-butyl-diphenyl-silanyloxy)-4-methyl-pentyl ester

Downstream raw materials:

(3R,4S,7S,8R)-9-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-4,8-dimethyl-nonanoic acid

(3R,4S,7S,8R)-9-Benzyloxy-7-(2,2-dimethyl-propionyloxy)-3-hydroxy-4,8-dimethyl-nonanoic acid