(E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Base Information

Chemical Name:(E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester
CAS No.:294198-66-6
Molecular Formula:C₃₂H₃₇Cl₃O₉
Molecular Weight:671.999
Hs Code.:

Synonyms:(E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

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Chemical Property of (E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

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Technology Process of (E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

There total 8 articles about (E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-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: 86.0%

: 294198-65-5
(E)-(4R,5S)-4-Benzyloxy-5-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

: 294198-66-6
(E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; at 80 ℃; for 12h;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

: 183625-29-8
methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate

: 294198-66-6
(E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / imidazole / dimethylformamide / 2.5 h / 0 - 20 °C

2: 2M aq. NaOH / methanol / 12 h / 20 °C

3: DCC; DMAP / CH₂Cl₂ / 72 h / 20 °C

4: 87 percent / aq. AcOH / tetrahydrofuran / 15 h / 70 - 110 °C

5: 75 percent / DCC; (+)-camphorsulfonic acid; DMAP / CH₂Cl₂ / 48 h / 20 °C

6: 79 percent / aq. AcOH / tetrahydrofuran / 48 h / 80 °C

7: 79 percent / DCC; DMAP; (+)-camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

8: 86 percent / aq. AcOH / tetrahydrofuran / 12 h / 80 °C

With 1H-imidazole; dmap; sodium hydroxide; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Hydrolysis / 3: Esterification / 4: desilylation / 5: Keck esterification / 6: desilylation / 7: Keck esterification / 8: desilylation;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

: 294198-49-5
(4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid

: 294198-66-6
(E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: DCC; DMAP / CH₂Cl₂ / 72 h / 20 °C

2: 87 percent / aq. AcOH / tetrahydrofuran / 15 h / 70 - 110 °C

3: 75 percent / DCC; (+)-camphorsulfonic acid; DMAP / CH₂Cl₂ / 48 h / 20 °C

4: 79 percent / aq. AcOH / tetrahydrofuran / 48 h / 80 °C

5: 79 percent / DCC; DMAP; (+)-camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

6: 86 percent / aq. AcOH / tetrahydrofuran / 12 h / 80 °C

With dmap; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Esterification / 2: desilylation / 3: Keck esterification / 4: desilylation / 5: Keck esterification / 6: desilylation;
DOI:10.1016/S0957-4166(00)00245-7