(2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

Base Information

• Chemical Name: (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one
• CAS No.: 405176-46-7
• Molecular Formula: C₃₂H₄₂O₇
• Molecular Weight: 538.681
• Mol file: 405176-46-7.mol

Synonyms:(2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

Chemical Property of (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

There total 20 articles about (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-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: 62.0%

(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxymethyl)-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one (405176-42-3) → (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one (405176-46-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol017271e DOI:10.1021/ja020635t

Reference yield:

(R)-2-(3,4-Dimethoxy-benzyloxymethyl)-oxirane (405176-39-8) → (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one (405176-46-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

1.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

1.3: 40 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

2.1: 96 percent / DCC; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 62 percent / HF*pyridine / tetrahydrofuran / 4 h / 20 °C

4.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.67 h / 20 °C

5.1: 72 percent / NaHMDS / tetrahydrofuran / -78 - 0 °C

6.1: 62 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; Dess-Martin periodane; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 5.1: Horner-Wadsworth-Emmons macrocyclization;

DOI:10.1021/ja020635t

Reference yield:

(2R,6R)-2-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-6-((E)-2-bromo-propenyl)-4-methylene-tetrahydro-pyran (389123-45-9) → (2E,8E,10Z,14E)-(1R,5R,13R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-13-hydroxy-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one (405176-46-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

1.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

1.3: 40 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

2.1: 96 percent / DCC; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 62 percent / HF*pyridine / tetrahydrofuran / 4 h / 20 °C

4.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.67 h / 20 °C

5.1: 72 percent / NaHMDS / tetrahydrofuran / -78 - 0 °C

6.1: 62 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; Dess-Martin periodane; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 5.1: Horner-Wadsworth-Emmons macrocyclization;

DOI:10.1021/ja020635t

upstream raw materials:

(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxymethyl)-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

(R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate

(R)-2-(3,4-Dimethoxy-benzyloxymethyl)-oxirane

(Z)-(R)-6-Benzyloxy-3-methyl-hex-2-ene-1,5-diol

Downstream raw materials:

(2E,8E,10Z,14E)-(1R,5R,17R)-5-(3,4-Dimethoxy-benzyloxymethyl)-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione