(E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

Base Information

Chemical Name:(E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester
CAS No.:455934-72-2
Molecular Formula:C₃₁H₄₅Cl₃O₈Si
Molecular Weight:680.138
Hs Code.:

Synonyms:(E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

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Chemical Property of (E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

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Technology Process of (E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

There total 7 articles about (E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl 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: 88.0%

: 105729-41-7,107493-76-5,101515-46-2
3-(R)-t-butyldimethylsilyloxybutanoic acid

: 455934-58-4
(E)-(4R,5S)-4-Benzyloxy-5-((E)-(S)-5-hydroxy-hex-2-enoyloxy)-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

: 455934-72-2
(E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

Guidance literature:: With dmap; (1S)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0957-4166(02)00180-5

Reference yield:

: 133522-12-0
(S,E)-5-((tert-butyldimethylsilyl)oxy)hex-2-enoic acid

: 455934-72-2
(E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 67 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

2: 93 percent / AcOH; H₂O / tetrahydrofuran / 5 h / 80 °C

3: 88 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 1 h / 20 °C

With dmap; (1S)-10-camphorsulfonic acid; water; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0957-4166(02)00180-5

Reference yield:

: 133522-08-4
methyl (2E,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-hexenoate

: 455934-72-2
(E)-(4R,5S)-4-Benzyloxy-5-{(E)-(S)-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoyloxy}-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / aq. NaOH / methanol / 12 h / 20 °C

2: 67 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3: 93 percent / AcOH; H₂O / tetrahydrofuran / 5 h / 80 °C

4: 88 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 1 h / 20 °C

With dmap; sodium hydroxide; (1S)-10-camphorsulfonic acid; water; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0957-4166(02)00180-5