(+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol

Base Information

Chemical Name:(+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol
CAS No.:145741-67-9
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:(+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol

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Chemical Property of (+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol

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Technology Process of (+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol

There total 3 articles about (+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-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: 17.0%

: 145741-66-8
(-)-(2E)-(4R,5S,6R)-5-Benzyloxy-4-tert-butyldimethylsilyloxy-7-(1',3'-dithiolan-2'-yl)-6-hydroxyhept-2-enoate

: 145741-67-9
(+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 34h; Heating;
DOI:10.1039/P19920002625

Reference yield:

: 145741-65-7
(-)-(2E)-(4R,5R,6R)-5-Benzyloxy-4,6-dihydroxy-7-(1',3'-dithiolan-2'-yl)hept-2-enoate

: 145741-67-9
(+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / imidazole, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

2: 17 percent / tributyltin hydride, AIBN / benzene / 34 h / Heating

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; benzene;
DOI:10.1039/P19920002625

Reference yield:

: 108788-48-3,108788-49-4,136838-95-4,136839-11-7,145741-63-5,145741-64-6
(Z)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acrylic acid ethyl ester

: 145741-67-9
(+)-(1S,2S,3R,4R)-Ethyl 5-benzyloxy-3-tert-butyldimethylsilyloxy-4-ethoxycarbonylmethylcyclopentan-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / ZnCl₂ / CH₂Cl₂ / 16 h

2: 100 percent / imidazole, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

3: 17 percent / tributyltin hydride, AIBN / benzene / 34 h / Heating

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; zinc(II) chloride; In dichloromethane; benzene;
DOI:10.1039/P19920002625