(Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadec-16-en-13-one

Base Information

• Chemical Name: (Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadec-16-en-13-one
• CAS No.: 457064-07-2
• Molecular Formula: C₂₇H₃₀O₆
• Molecular Weight: 450.532

Synonyms:(Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadec-16-en-13-one

Chemical Property of (Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadec-16-en-13-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadec-16-en-13-one

There total 4 articles about (Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadec-16-en-13-one 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: 71.0%

(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 (457064-30-1) → (Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.03,8]octadec-16-en-13-one (457064-07-2)

Guidance literature:

(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; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃;

With dmap; In benzene; at 80 ℃; Further stages.;

DOI:10.1021/ol026306n

Reference yield:

2-((2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-ethanol (457064-28-7) → (Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.03,8]octadec-16-en-13-one (457064-07-2)

Guidance literature:

Multi-step reaction with 3 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

3.1: 2,4,6-Cl₃C₆H₂COCl; Et₃N / tetrahydrofuran / 20 °C

3.2: 71 percent / DMAP / benzene / 80 °C

With barium dihydroxide; pyridine-SO₃ complex; 2,4,6-trichlorobenzoyl chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1021/ol026306n

Reference yield:

(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 (457064-29-8) → (Z)-(1S,3R,6R,8S,9R,11R)-9-Benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.03,8]octadec-16-en-13-one (457064-07-2)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 88 percent / CSA / CH₂Cl₂; methanol / 20 °C

2.1: 2,4,6-Cl₃C₆H₂COCl; Et₃N / tetrahydrofuran / 20 °C

2.2: 71 percent / DMAP / benzene / 80 °C

With barium dihydroxide; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/ol026306n

upstream raw materials:

(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

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

(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

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

Downstream raw materials:

Phosphoric acid (13E,16Z)-(1S,3R,6R,8S,9R,11R)-9-benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.0^3,8]octadeca-13,16-dien-13-yl ester diphenyl ester

C₅₄H₇₀O₁₇S

C₅₄H₇₀O₁₅S

C₅₄H₇₈O₁₁Si

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