(+)-dibenzyl macrosphelide A

Base Information

Chemical Name:(+)-dibenzyl macrosphelide A
CAS No.:294198-64-4
Molecular Formula:C₃₀H₃₄O₈
Molecular Weight:522.595
Hs Code.:

Synonyms:

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Chemical Property of (+)-dibenzyl macrosphelide A

Chemical Property:

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Technology Process of (+)-dibenzyl macrosphelide A

There total 10 articles about (+)-dibenzyl macrosphelide A 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:

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

: 294198-64-4
(+)-dibenzyl macrosphelide A

Guidance literature:: (E)-(4S,5R)-4-Benzyloxy-5-[(E)-(4S,5R)-4-benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid; With 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; triethylamine; at 20 ℃; for 3h;

With dmap; In toluene; at 100 ℃; for 24h;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

: 183625-23-2
methyl (4S,5R)-4-benzyloxy-5-hydroxy-2(E)-hexenoate

: 294198-64-4
(+)-dibenzyl macrosphelide A

Guidance literature:: Multi-step reaction with 10 steps

1.1: imidazole / dimethylformamide / 2.5 h / 0 - 20 °C

2.1: 2M aq. NaOH / methanol / 12 h / 20 °C

3.1: DCC; DMAP / CH₂Cl₂ / 72 h / 20 °C

4.1: aq. AcOH / tetrahydrofuran / 15 h / 70 - 110 °C

5.1: 66 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 48 h / 20 °C

6.1: 90 percent / aq. AcOH / tetrahydrofuran / 48 h / 80 °C

7.1: 88 percent / DCC; DMAP; (+)-comphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

8.1: 67 percent / aq. AcOH / tetrahydrofuran / 3 h / 80 °C

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

10.1: 2,4,6-trichlorbenzoyl chloride; 4A mol. sieves; Et₃N / 3 h / 20 °C

10.2: DMAP / toluene / 24 h / 100 °C

With 1H-imidazole; dmap; sodium hydroxide; (+)-comphorsulfonic acid; 4 A molecular sieve; AcOH-AcONa buffer; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Hydrolysis / 3.1: Esterification / 4.1: desilylation / 5.1: Keck esterification / 6.1: desilylation / 7.1: Keck esterification / 8.1: desilylation / 9.1: reductive hydrolysis / 10.1: activation / 10.2: Cyclization;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

: (E)-(4S,5R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

: 294198-64-4
(+)-dibenzyl macrosphelide A

Guidance literature:: Multi-step reaction with 9 steps

1.1: 2M aq. NaOH / methanol / 12 h / 20 °C

2.1: DCC; DMAP / CH₂Cl₂ / 72 h / 20 °C

3.1: aq. AcOH / tetrahydrofuran / 15 h / 70 - 110 °C

4.1: 66 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 48 h / 20 °C

5.1: 90 percent / aq. AcOH / tetrahydrofuran / 48 h / 80 °C

6.1: 88 percent / DCC; DMAP; (+)-comphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

7.1: 67 percent / aq. AcOH / tetrahydrofuran / 3 h / 80 °C

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

9.1: 2,4,6-trichlorbenzoyl chloride; 4A mol. sieves; Et₃N / 3 h / 20 °C

9.2: DMAP / toluene / 24 h / 100 °C

With dmap; sodium hydroxide; (+)-comphorsulfonic acid; 4 A molecular sieve; AcOH-AcONa buffer; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; methanol; dichloromethane; 1.1: Hydrolysis / 2.1: Esterification / 3.1: desilylation / 4.1: Keck esterification / 5.1: desilylation / 6.1: Keck esterification / 7.1: desilylation / 8.1: reductive hydrolysis / 9.1: activation / 9.2: Cyclization;
DOI:10.1016/S0957-4166(00)00245-7