(2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal

Base Information

• Chemical Name: (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal
• CAS No.: 444109-42-6
• Molecular Formula: C₂₀H₃₄O₃Si
• Molecular Weight: 350.574
• Mol file: 444109-42-6.mol

Synonyms:(2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal

Chemical Property of (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal

There total 12 articles about (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal 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%

(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol (100649-11-4) → (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal (444109-42-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1016/S0957-4166(02)00178-7

Reference yield: 93.0%

(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione (876954-51-7) → (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal (444109-42-6)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.166667h;

DOI:10.1021/ol052900w

Reference yield:

(3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester (444109-26-6) → (2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal (444109-42-6)

Guidance literature:

(3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester; With ozone; In methanol; at -78 ℃;

With dimethylsulfide; In methanol; at -78 - 0 ℃;

DOI:10.1021/ja043168j

upstream raw materials:

(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

(3E,5S,6R,7S)-8-benzyloxy-6-(tert-butyldimethylsilanyloxy)-5,7-dimethyl-oct-3-enoic acid methyl ester

(S)-N-[(2R,3S,4S)-5-benzyloxy-3-tert-butyldimethylsilyloxy-2,4-dimethylpentanoyl]-4-isopropyl-1,3-thiazolidine-2-thione

t-butyldimethylsiyl triflate

Downstream raw materials:

[(1R,2S)-1-((S)-2-Benzyloxy-1-methyl-ethyl)-2,4-dimethyl-pent-3-enyloxy]-tert-butyl-dimethyl-silane

(2S,3R,4S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)-6,6-dibromo-2,4-dimethyl-hex-5-ene

(5S,6R)-6-[(1S)-2-benzyloxy-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one

(5S,6R)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-methyl-5,6-dihydro-2H-pyran-2-ol