Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester
• CAS No.: 214198-25-1
• Molecular Formula: C₃₈H₆₈O₇Si₂
• Molecular Weight: 693.125
• Mol file: 214198-25-1.mol

Synonyms:Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester

Chemical Property of Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester

There total 2 articles about Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl 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:

(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal (116660-67-4,122330-69-2,149250-62-4,97848-38-9) + Benzoic acid (1R,2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-allyl)-2,4-dimethyl-5-trimethylsilanyloxy-hex-5-enyl ester (442899-82-3) → Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester (214198-25-1)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1021/ja017885e

Reference yield:

Benzoic acid (1R,2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-allyl)-2,4-dimethyl-5-oxo-hexyl ester → Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester (214198-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / LiN(TMS)2; Et₃N / tetrahydrofuran / -78 °C

2: BF₃*Et₂O; 4 Angstroem sieves / CH₂Cl₂ / -78 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja017885e

Reference yield: 75.0%

Benzoic acid (1R,2R,3R,4S,7R,8S,9R)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1-((S)-1-methoxy-allyl)-2,4,8,10-tetramethyl-5-oxo-undecyl ester (214198-25-1) → Benzoic acid (1R,2S,3R,4S)-4-((2R,4R,5S,6R)-2,4-dihydroxy-6-isopropyl-5-methyl-tetrahydro-pyran-2-yl)-3-hydroxy-1-((S)-1-methoxy-allyl)-2-methyl-pentyl ester

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; In N,N-dimethyl-formamide; at 23 ℃;

DOI:10.1021/jo981215i

upstream raw materials:

(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal

Benzoic acid (1R,2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-allyl)-2,4-dimethyl-5-trimethylsilanyloxy-hex-5-enyl ester