(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid

Base Information

Chemical Name:(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid
CAS No.:457064-30-1
Molecular Formula:C₂₇H₃₂O₇
Molecular Weight:468.547
Hs Code.:

Synonyms:(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid

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Chemical Property of (Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid

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Technology Process of (Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid

There total 3 articles about (Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-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: 88.0%

: 457064-29-8
(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid ethyl ester

: 457064-30-1
(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid

Guidance literature:: (Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid ethyl ester; With barium dihydroxide; In 1,4-dioxane; water; at 60 ℃;

With camphor-10-sulfonic acid; In methanol; dichloromethane; at 20 ℃; Further stages.;
DOI:10.1021/ol026306n

Reference yield:

: 457064-28-7
2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol

: 457064-30-1
(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: SO₃*Pyr; Et₃N; DMSO / CH₂Cl₂ / 0 °C

1.2: KHMDS / tetrahydrofuran / 0 h / -78 °C

2.1: Ba(OH)2*8H₂O / dioxane; H₂O / 60 °C

2.2: 88 percent / CSA / CH₂Cl₂; methanol / 20 °C

With barium dihydroxide; pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; dichloromethane; water;
DOI:10.1021/ol026306n

Reference yield:

: 342901-72-8
(2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-6-(2-hydroxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

: 457064-30-1
(Z)-6-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-7-hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-hex-4-enoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: DMAP / CH₂Cl₂ / 0 °C

1.2: 83 percent / PPTS / CH₂Cl₂; methanol / 0 °C

2.1: SO₃*Pyr; Et₃N; DMSO / CH₂Cl₂ / 0 °C

2.2: KHMDS / tetrahydrofuran / 0 h / -78 °C

3.1: Ba(OH)2*8H₂O / dioxane; H₂O / 60 °C

3.2: 88 percent / CSA / CH₂Cl₂; methanol / 20 °C

With dmap; barium dihydroxide; pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; dichloromethane; water;
DOI:10.1021/ol026306n