Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester
• CAS No.: 171019-26-4
• Molecular Formula: C₂₂H₃₈O₄Si
• Molecular Weight: 394.627
• Mol file: 171019-26-4.mol

Synonyms:Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester

Chemical Property of Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester

There total 2 articles about Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl 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: 75.0%

benzyl 2,2,2-trifluoroacetimidate + acetic acid (2S,3R,4R)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-2,4-dimethylpentyl ester (171019-25-3) → Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester (171019-26-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In hexane; dichloromethane;

DOI:10.1016/0957-4166(95)00272-Q

Reference yield:

(2R,3s,4S)-3-[(tert-butyl-dimethylsilyl)oxy]-2,4-dimethylpentane-1,5-diol (127808-53-1,127808-54-2,127910-49-0) → Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester (171019-26-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / hexane / Ambient temperature; Candida rugosa lipase

2: 75 percent / TMSOTf / CH₂Cl₂; hexane

With trimethylsilyl trifluoromethanesulfonate; In hexane; dichloromethane;

DOI:10.1016/0957-4166(95)00272-Q

Reference yield: 90.0%

Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester (171019-26-4) → 5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol (105816-26-0)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1016/0957-4166(95)00272-Q

upstream raw materials:

acetic acid (2S,3R,4R)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-2,4-dimethylpentyl ester

(2R,3s,4S)-3-[(tert-butyl-dimethylsilyl)oxy]-2,4-dimethylpentane-1,5-diol

Downstream raw materials:

5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol

(2S,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol acetonide