(2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol

Base Information

• Chemical Name: (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol
• CAS No.: 183888-77-9
• Molecular Formula: C₄₃H₅₂O₄Si₂
• Molecular Weight: 689.054
• Mol file: 183888-77-9.mol

Synonyms:(2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol

Chemical Property of (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol

There total 8 articles about (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol 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: 95.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2S,3S)-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(phenylmethoxy)butane-1,2-diol (143326-16-3) → (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol (183888-77-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 18h; Ambient temperature;

Reference yield: 90.0%

2-O-benzyl-L-threitol (84379-51-1,84379-52-2,124909-02-0,127000-44-6) + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol (183888-77-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 24h;

DOI:10.1016/S0040-4020(03)00692-6

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2S,3S)-(+)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-ol (183888-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / p-TsOH / 8 h

2: 81.5 percent / LiALH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / -20 - 50 °C

3: 90 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 °C

With pyridine; dmap; lithium aluminium tetrahydride; aluminium trichloride; toluene-4-sulfonic acid; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(03)00692-6

upstream raw materials:

tert-butylchlorodiphenylsilane

(2S,3S)-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(phenylmethoxy)butane-1,2-diol

2-O-benzyl-L-threitol

benzaldehyde dimethyl acetal

Downstream raw materials:

(3R)-3-benzyloxy-1,4-bis(tert-butyl-diphenyl-silyloxy)butan-2-one