(2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal

Base Information

• Chemical Name: (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal
• CAS No.: 888488-09-3
• Molecular Formula: C₂₃H₄₀O₄Si
• Molecular Weight: 408.654
• Mol file: 888488-09-3.mol

Synonyms:(2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal

Chemical Property of (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal

There total 8 articles about (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal 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%

(2R,3R,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptan-1-ol (888488-34-4) → (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal (888488-09-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol060347s

Reference yield:

(4R,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one (888488-12-8) → (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal (888488-09-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / NaBH₄ / ethanol / 5 h / 0 - 20 °C

2: 84 percent / trifluoromethanesulfonic acid / diethyl ether / 0 - 20 °C

3: 87 percent / H₂ / W-2 Raney nickel / ethanol / 6 h / 20 °C

4: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With sodium tetrahydroborate; trifluorormethanesulfonic acid; hydrogen; Dess-Martin periodane; W-2 Raney nickel; In diethyl ether; ethanol; dichloromethane; 4: Dess-Martin oxidation;

DOI:10.1021/ol060347s

Reference yield:

(3S,4S,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-ol (888488-14-0) → (2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal (888488-09-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / trifluoromethanesulfonic acid / diethyl ether / 0 - 20 °C

2: 87 percent / H₂ / W-2 Raney nickel / ethanol / 6 h / 20 °C

3: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With trifluorormethanesulfonic acid; hydrogen; Dess-Martin periodane; W-2 Raney nickel; In diethyl ether; ethanol; dichloromethane; 3: Dess-Martin oxidation;

DOI:10.1021/ol060347s

upstream raw materials:

(2R,3R,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptan-1-ol

(4R,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one

(3S,4S,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-ol

(3S,4S,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-3-(p-methoxybenzyloxy)-4,6-dimethylheptane

Downstream raw materials:

(3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione

(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one