(2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal

Base Information

• Chemical Name: (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal
• CAS No.: 618095-90-2
• Molecular Formula: C₂₄H₃₄O₃Si
• Molecular Weight: 398.618
• Mol file: 618095-90-2.mol

Synonyms:(2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal

Chemical Property of (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal

There total 4 articles about (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal 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: 94.0%

tert-butyl((2R,3S,4S,E)-6-cyclohexyl-3-methoxy-2,4-dimethylhex-5-enyloxy)diphenylsilane (1017246-21-7) → (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal (618095-90-2)

Guidance literature:

tert-butyl((2R,3S,4S,E)-6-cyclohexyl-3-methoxy-2,4-dimethylhex-5-enyloxy)diphenylsilane; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃; for 7h;

DOI:10.1021/ol702989g

Reference yield: 85.0%

(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol (618096-13-2) → (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal (618095-90-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol035227o

Reference yield:

(2R,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol (108393-30-2) → (2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal (618095-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMAP; imidazole / CH₂Cl₂ / 0.5 h / 20 °C

1.2: NaH; TBAI / tetrahydrofuran / 16 h / 60 °C

1.3: 6.5 g / AlCl₃ / m-xylene; CH₂Cl₂ / 1 h / -40 - -20 °C

2.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 2.1: Swern oxidation;

DOI:10.1021/ol035227o

upstream raw materials:

(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

(2R,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol

tert-butylchlorodiphenylsilane

tert-butyl((2R,3S,4S,E)-6-cyclohexyl-3-methoxy-2,4-dimethylhex-5-enyloxy)diphenylsilane

Downstream raw materials:

(4S,5R,6S,7R,8R,Z)-9-((tert-butyldiphenylsilyl)oxy)-4-(dimethyl(phenyl)silyl)-7-methoxy-6,8-dimethylnon-2-en-5-ol

C₂₈H₄₀O₂Si

C₃₆H₅₂O₃Si₂

C₃₆H₅₂O₃Si₂