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

Base Information

• Chemical Name: 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
• CAS No.: 457064-08-3
• Molecular Formula: C₃₉H₃₉O₉P
• Molecular Weight: 682.707

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 5 articles about 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 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:

chlorophosphoric acid diphenyl ester (2524-64-3) + (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) → Phosphoric acid (13E,16Z)-(1S,3R,6R,8S,9R,11R)-9-benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.03,8]octadeca-13,16-dien-13-yl ester diphenyl ester (457064-08-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.666667h;

DOI:10.1021/ol026306n

Reference yield:

(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) → Phosphoric acid (13E,16Z)-(1S,3R,6R,8S,9R,11R)-9-benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.03,8]octadeca-13,16-dien-13-yl ester diphenyl ester (457064-08-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,4,6-Cl₃C₆H₂COCl; Et₃N / tetrahydrofuran / 20 °C

1.2: 71 percent / DMAP / benzene / 80 °C

2.1: 6.39 g / potassium hexamethyldisilazide; hexamethylphosphoric triamide / tetrahydrofuran; toluene / 0.67 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; toluene;

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) → Phosphoric acid (13E,16Z)-(1S,3R,6R,8S,9R,11R)-9-benzyloxy-6-phenyl-2,5,7,12-tetraoxa-tricyclo[9.7.0.03,8]octadeca-13,16-dien-13-yl ester diphenyl ester (457064-08-3)

Guidance literature:

Multi-step reaction with 3 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

3.1: 6.39 g / potassium hexamethyldisilazide; hexamethylphosphoric triamide / tetrahydrofuran; toluene / 0.67 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; barium dihydroxide; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; toluene;

DOI:10.1021/ol026306n

upstream raw materials:

chlorophosphoric acid diphenyl ester

(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

(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

Downstream raw materials:

C₃₂H₃₈O₉

C₃₁H₃₈O₈

C₃₁H₄₀O₉

(1S,3R,7S,9R,10S,12R,14R,15S,16R)-9,14-Bis-benzyloxy-10-benzyloxymethyl-16-hydroxymethyl-5,5-dimethyl-4,6,11,17-tetraoxa-tricyclo[10.5.0.0^3,7]heptadecan-15-ol

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