(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

Base Information

Chemical Name:(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid
CAS No.:294198-56-4
Molecular Formula:C₃₀H₃₆O₉
Molecular Weight:540.61
Hs Code.:

Synonyms:(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

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Chemical Property of (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

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Technology Process of (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

There total 9 articles about (E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid 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:

: 294198-55-3
(E)-(4R,5S)-4-Benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

: 294198-56-4
(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

Guidance literature:: With AcOH-AcONa buffer; zinc; In tetrahydrofuran; at 20 ℃; for 2.5h;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

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

: 294198-56-4
(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

Guidance literature:: Multi-step reaction with 9 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; (+)-comphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

8: 96 percent / aq. AcOH / tetrahydrofuran / 3 h / 80 °C

9: Zn dust; aq. AcOH-AcONa buffer / tetrahydrofuran / 2.5 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; (+)-comphorsulfonic acid; AcOH-AcONa buffer; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; zinc; 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 / 9: reductive hydrolysis;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

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

: 294198-56-4
(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

Guidance literature:: Multi-step reaction with 7 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; (+)-comphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

6: 96 percent / aq. AcOH / tetrahydrofuran / 3 h / 80 °C

7: Zn dust; aq. AcOH-AcONa buffer / tetrahydrofuran / 2.5 h / 20 °C

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