ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate

Base Information

• Chemical Name: ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate
• CAS No.: 1312759-10-6
• Molecular Formula: C₃₂H₄₄O₅Si
• Molecular Weight: 536.784
• Mol file: 1312759-10-6.mol

Synonyms:ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate

Chemical Property of ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate

There total 6 articles about ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate 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: 91.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexanal (1312759-09-3) → ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate (1312759-10-6)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; for 0.25h; Inert atmosphere;

(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexanal; In tetrahydrofuran; at 0 - 25 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.02.008

Reference yield:

(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexan-1-ol (1312759-08-2) → ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate (1312759-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 3 h / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / Inert atmosphere

2.2: 18 h / 0 - 25 °C / Inert atmosphere

With sodium acetate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 2.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetasy.2011.02.008

Reference yield:

(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene (1197010-57-3) → ethyl (2E,6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octenoate (1312759-10-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

1.2: 15 h / 0 - 25 °C

2.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 3 h / 0 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.25 h / Inert atmosphere

3.2: 18 h / 0 - 25 °C / Inert atmosphere

With dimethylsulfide borane complex; sodium acetate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 3.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetasy.2011.02.008

upstream raw materials:

(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene

(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexan-1-ol

diethoxyphosphoryl-acetic acid ethyl ester

(4S,5R)-4-tert-butyldiphenylsilyloxy-5,6-(cyclohexylidenedioxy)hexanal

Downstream raw materials:

ethyl (6S)-6-tert-butyldiphenylsilyloxyoct-7-enoate

ethyl (6S,7E,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxyoctadecenoate

ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-(cyclohexylidenedioxy)octanoate

ethyl (6S,7R)-6-tert-butyldiphenylsilyloxy-7,8-dihydroxyoctanoate

Refernces