[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

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Chemical Name:[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester
CAS No.:940877-36-1
Molecular Formula:C₃₉H₄₉ClO₅Si
Molecular Weight:661.354
Hs Code.:

[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

Synonyms:[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

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Chemical Property of [(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

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Technology Process of [(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

There total 7 articles about [(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic 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: 85.0%

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

: 940877-34-9
[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid

: 940877-36-1
[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester

Guidance literature:: With dmap; 4-(dimethylamino)pyridine hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 50 ℃; for 36h;
DOI:10.1021/ol070573h

Reference yield:

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

: 940877-36-1
[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic 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: 85 percent / DMAP*HCl; DMAP; EDCI / tetrahydrofuran / 36 h / 50 °C

With dmap; 4 A molecular sieve; (S)-[1,1']-binaphthalenyl-2,2'-diol; 4-(dimethylamino)pyridine hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; titanium(IV) isopropylate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol070573h

Reference yield:

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

: 940877-36-1
[(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic 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: 85 percent / DMAP*HCl; DMAP; EDCI / tetrahydrofuran / 36 h / 50 °C

With dmap; oxalyl dichloride; 4 A molecular sieve; (S)-[1,1']-binaphthalenyl-2,2'-diol; 4-(dimethylamino)pyridine hydrochloride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; titanium(IV) isopropylate; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;
DOI:10.1021/ol070573h