(2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal

Base Information

• Chemical Name: (2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal
• CAS No.: 878006-96-3
• Molecular Formula: C₂₁H₃₄O₃Si
• Molecular Weight: 362.585
• Mol file: 878006-96-3.mol

Synonyms:(2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal

Chemical Property of (2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal

There total 5 articles about (2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal 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: 95.0%

C21H36O3Si → (2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal (878006-96-3)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1055/s-0035-1561614

Reference yield:

(2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-ene-1,1-diol → (2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal (878006-96-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃;

DOI:10.1055/s-2005-922789

Reference yield:

(3R,4R)-4-Benzyloxymethyl-3-methyl-2-oxo-hex-5-enoic acid methyl ester (878006-89-4) → (2R,3R,4R)-4-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-hex-5-enal (878006-96-3)

Guidance literature:

Multi-step reaction with 4 steps

1: K[(sec-Bu)3BH] / tetrahydrofuran / 0.17 h / -100 °C

2: 2,6-lutidine / CH₂Cl₂ / 0 °C

3: DIBAL-H / CH₂Cl₂ / -78 - 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 4: Dess-Martin oxidation;

DOI:10.1055/s-2005-922789

upstream raw materials:

(3R,4R)-4-Benzyloxymethyl-3-methyl-2-oxo-hex-5-enoic acid methyl ester

(2R,3R,4R)-4-Benzyloxymethyl-2-hydroxy-3-methyl-hex-5-enoic acid methyl ester