(-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

Base Information

• Chemical Name: (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester
• CAS No.: 862877-69-8
• Molecular Formula: C₂₃H₃₅O₈P
• Molecular Weight: 470.5
• Mol file: 862877-69-8.mol

Synonyms:(-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

Chemical Property of (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester

There total 9 articles about (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-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: 93.0%

(-)-(2S,6E)-8-benzyloxy-2-hydroxy-2,6-dimethyloct-6-en-3-one (862877-68-7) + diethylphosphonoacetic acid (3095-95-2) → (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester (862877-69-8)

Guidance literature:

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

DOI:10.1016/j.tet.2005.05.050

Reference yield:

(-)-(2'S,1R,4E)-6-benzyloxy-4-methyl-1-(2'-methyloxiranyl)-hex-4-en-1-ol (862877-65-4) → (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester (862877-69-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Ti(O-iPr)4 / CH₂Cl₂ / 20 °C

2: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 97 percent / aq. NaOH / methanol / 12 h / 20 °C

4: 93 percent / DCC / CH₂Cl₂ / 0.5 h / 20 °C

With titanium(IV) isopropylate; sodium hydroxide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 2: Swern oxidation;

DOI:10.1016/j.tet.2005.05.050

Reference yield:

(+)-(2S,3R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2,3-dihydroxy-2,6-dimethyl-oct-6-enyl ester (862877-73-4) → (-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2-hydroxy-2,6-dimethyl-3-oxo-oct-6-enyl ester (862877-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 97 percent / aq. NaOH / methanol / 12 h / 20 °C

3: 93 percent / DCC / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hydroxide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1: Swern oxidation;

DOI:10.1016/j.tet.2005.05.050

upstream raw materials:

(-)-(2S,6E)-8-benzyloxy-2-hydroxy-2,6-dimethyloct-6-en-3-one

diethylphosphonoacetic acid

(-)-(2'S,1R,4E)-6-benzyloxy-4-methyl-1-(2'-methyloxiranyl)-hex-4-en-1-ol

(+)-(2S,3R,6E)-2,2-dimethylpropionic acid 8-benzyloxy-2,3-dihydroxy-2,6-dimethyl-oct-6-enyl ester

Downstream raw materials:

(-)-(2S,6E)-(diethoxyphosphoryl)acetic acid 8-benzyloxy-2,6-dimethyl-3-oxo-2-trimethylsilanyloxy-oct-6-enyl ester