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

Base Information

• Chemical Name: (Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester
• CAS No.: 405176-41-2
• Molecular Formula: C₄₈H₈₃O₁₁PSi₂
• Molecular Weight: 923.325
• Mol file: 405176-41-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl 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: 96.0%

diethylphosphonoacetic acid (3095-95-2) + (E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol (405176-40-1) → (Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester (405176-41-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ol017271e DOI:10.1021/ja020635t

Reference yield:

(R)-2-(3,4-Dimethoxy-benzyloxymethyl)-oxirane (405176-39-8) → (Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester (405176-41-2)

Guidance literature:

Multi-step reaction with 2 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

With dmap; tert.-butyl lithium; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane; pentane;

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) → (Diethoxy-phosphoryl)-acetic acid (E)-(R)-4-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxymethyl)-3-methyl-but-3-enyl ester (405176-41-2)

Guidance literature:

Multi-step reaction with 2 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

With dmap; tert.-butyl lithium; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane; pentane;

DOI:10.1021/ja020635t

upstream raw materials:

diethylphosphonoacetic acid

(E)-(R)-5-{(2R,6R)-6-[(2E,6Z)-(R)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-(3,4-dimethoxy-benzyloxy)-4-methyl-pent-4-en-2-ol

t-butyldimethylsiyl triflate

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

Downstream raw materials:

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

(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

(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