(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

Base Information

• Chemical Name: (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
• CAS No.: 405176-42-3
• Molecular Formula: C₃₈H₅₆O₇Si
• Molecular Weight: 652.944
• Mol file: 405176-42-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 19 articles about (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 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: 72.0%

(Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-8-oxo-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester (405176-38-7) → (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)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1021/ja020635t

Reference yield:

(R)-2-(3,4-Dimethoxy-benzyloxymethyl)-oxirane (405176-39-8) → (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)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; dmap; 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)-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)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; dmap; 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:

(Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-8-oxo-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester

(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

(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