(1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester

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Chemical Name:(1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester
CAS No.:264132-24-3
Molecular Formula:C₂₆H₃₄O₆
Molecular Weight:442.552
Hs Code.:

Synonyms:(1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester

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Chemical Property of (1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester

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Technology Process of (1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester

There total 1 articles about (1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl 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: 59.0%

: 15799-66-3,17421-59-9,57682-80-1
trans-β-triphenylstannylstyrene

: ((1S,2S)-2-Benzyloxymethoxy-1-formyl-propoxy)-acetic acid tert-butyl ester

: 264132-24-3
(1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester

Guidance literature:: With copper(l) iodide; tributylphosphine; phenyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃;
DOI:10.1021/jo991681n

Reference yield:

: 264132-24-3
(1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester

: C₄₂H₄₈O₉

Guidance literature:: Multi-step reaction with 11 steps

1.1: trifluoroacetic acid / benzene / 0.5 h / Heating

2.1: LiHMDS; Me₃SiCl; Et₃N / hexane; tetrahydrofuran / 2 h / -78 °C

2.2: 70 mg / HCl / H₂O / pH 2

3.1: 97 percent / DMAP; DIC; TFA / CH₂Cl₂ / 40 °C

4.1: 81 percent / BF₃-Et₂O; Me₂S / CH₂Cl₂ / 0.17 h / 0 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h

5.2: 84 percent / DMAP / benzene / 2 h

6.1: 85 percent / BF₃-Et₂O; Me₂S / CH₂Cl₂ / 0.17 h / 0 °C

7.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h

7.2: 95 percent / DMAP; Et₃N / benzene / 2 h

8.1: 88 percent / BF₃-Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

9.1: 96 percent / phosphate buffer; zinc dust / H₂O; tetrahydrofuran / 4 h

10.1: 76 percent / DMAP; DMAP-TFA; DIC / CHCl₃ / 9 h / Heating

11.1: 89 percent / H₂ / palladium(II) hydroxide / ethyl acetate / 12 h / 760.05 Torr

With dmap; chloro-trimethyl-silane; phosphate buffer; dimethylsulfide; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; hydrogen; dacarbazine; 4-N,N-dimethylaminopyridine trifluoroacetate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; zinc; palladium dihydroxide; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; ethyl acetate; benzene; 1.1: Cyclization / 2.1: Rearrangement / 2.2: Hydrolysis / 3.1: Esterification / 4.1: Hydrolysis / 5.1: Substitution / 5.2: Substitution / 6.1: Hydrolysis / 7.1: Substitution / 7.2: Substitution / 8.1: Hydrolysis / 9.1: Reduction / 10.1: Cyclization / 11.1: Hydrogenation;
DOI:10.1021/jo991681n

Reference yield:

: 264132-24-3
(1S,2S,3E)-1-[(1S)-1-benzyloxymethoxyethyl]-2-hydroxy-4-phenylbut-3-enyloxyacetic acid tert-butyl ester

: 264132-51-6
C₅₂H₅₃Cl₃O₁₁

Guidance literature:: Multi-step reaction with 7 steps

1.1: trifluoroacetic acid / benzene / 0.5 h / Heating

2.1: LiHMDS; Me₃SiCl; Et₃N / hexane; tetrahydrofuran / 2 h / -78 °C

2.2: 70 mg / HCl / H₂O / pH 2

3.1: 97 percent / DMAP; DIC; TFA / CH₂Cl₂ / 40 °C

4.1: 81 percent / BF₃-Et₂O; Me₂S / CH₂Cl₂ / 0.17 h / 0 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h

5.2: 84 percent / DMAP / benzene / 2 h

6.1: 85 percent / BF₃-Et₂O; Me₂S / CH₂Cl₂ / 0.17 h / 0 °C

7.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h

7.2: 95 percent / DMAP; Et₃N / benzene / 2 h

With dmap; chloro-trimethyl-silane; dimethylsulfide; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; dacarbazine; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; benzene; 1.1: Cyclization / 2.1: Rearrangement / 2.2: Hydrolysis / 3.1: Esterification / 4.1: Hydrolysis / 5.1: Substitution / 5.2: Substitution / 6.1: Hydrolysis / 7.1: Substitution / 7.2: Substitution;
DOI:10.1021/jo991681n