3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

Base Information

Chemical Name:3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester
CAS No.:940877-21-4
Molecular Formula:C₃₃H₄₁ClO₄Si
Molecular Weight:565.225
Hs Code.:

Synonyms:3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

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Chemical Property of 3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

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Technology Process of 3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

There total 6 articles about 3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl 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: 94.0%

: 940877-17-8
(S)-1-(tert-butyl-diphenyl-silyloxy)-5-chloromethyl-hex-5-en-3-ol

: 27912-85-2
3-(benzyloxy)propanoic acid

: 940877-21-4
3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

Guidance literature:: With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide; In chloroform; at 20 ℃; for 14h;
DOI:10.1021/ol070573h

Reference yield:

: 112897-03-7
3-(tert-butyldiphenylsilyloxy)-1-propanal

: 940877-21-4
3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / (S)-BINOL; 4 Angstroem molecular sieves; CF₃CO₂H / titanium(IV) isopropoxide / CH₂Cl₂ / 72.5 h / -78 - -20 °C

2: 94 percent / DMAP*HCl; DMAP; DCC / CHCl₃ / 14 h / 20 °C

With dmap; 4 A molecular sieve; (S)-[1,1']-binaphthalenyl-2,2'-diol; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; titanium(IV) isopropylate; In dichloromethane; chloroform;
DOI:10.1021/ol070573h

Reference yield:

: 127047-71-6
3-(tert-butyldiphenylsilyloxy)propan-1-ol

: 940877-21-4
3-benzyloxy-propionic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.67 h / -78 - -20 °C

2: 83 percent / (S)-BINOL; 4 Angstroem molecular sieves; CF₃CO₂H / titanium(IV) isopropoxide / CH₂Cl₂ / 72.5 h / -78 - -20 °C

3: 94 percent / DMAP*HCl; DMAP; DCC / CHCl₃ / 14 h / 20 °C

With dmap; oxalyl dichloride; 4 A molecular sieve; (S)-[1,1']-binaphthalenyl-2,2'-diol; 4-(dimethylamino)pyridine hydrochloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; titanium(IV) isopropylate; In dichloromethane; chloroform; 1: Swern oxidation;
DOI:10.1021/ol070573h