methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Base Information

• Chemical Name: methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate
• CAS No.: 124887-12-3
• Molecular Formula: C₂₄H₃₄O₄Si
• Molecular Weight: 414.617
• Mol file: 124887-12-3.mol

Synonyms:methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Chemical Property of methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

There total 3 articles about methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate 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: 78.0%

methyl 3,5-dihydoxy-2,4-dimethylpentanoate (105365-06-8) → methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate (124887-12-3) + (3R,4S,5R)-4-hydroxy-3,5-dimethyl-tetrahydro-(2H)-pyran-2-one (89395-27-7)

Guidance literature:

With 1H-imidazole; 4 A molecular sieve; tert-butylchlorodiphenylsilane; In N,N-dimethyl-formamide; Ambient temperature; overnight;

DOI:10.1055/s-1991-26485

Reference yield: 15.0%

methyl 3,5-dihydoxy-2,4-dimethylpentanoate (105365-06-8) + tert-butylchlorodiphenylsilane (58479-61-1) → methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate (124887-12-3) + (3R,4S,5R)-4-hydroxy-3,5-dimethyl-tetrahydro-(2H)-pyran-2-one (89395-27-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)93717-7

Reference yield:

1-methyl hydrogen (3S,2R,4S)-3-hydroxy-2,4-dimethylglutarate (89329-05-5) → methyl (2R,3S,4R)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate (124887-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.408 g / borane-dimethyl sulfide complex / tetrahydrofuran / 1) -10 deg C, 1.5 h 2) r.t, 3 h

2: 78 percent / t-BuPh₂SiCl, molecular sieves 4 Angstroem, imidazole / dimethylformamide / Ambient temperature; overnight

With 1H-imidazole; dimethylsulfide borane complex; 4 A molecular sieve; tert-butylchlorodiphenylsilane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1055/s-1991-26485

upstream raw materials:

methyl 3,5-dihydoxy-2,4-dimethylpentanoate

tert-butylchlorodiphenylsilane

1-methyl hydrogen (3S,2R,4S)-3-hydroxy-2,4-dimethylglutarate

Downstream raw materials:

(2S,3R,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentane-1,3-diol

2',6'-dimethylphenyl (2R,3R,4R,5R,6S)-3-hydroxy-5,7-isopropylidenedioxy-2,4,6-trimethylheptanonate

(2R,3R,4S)-1-(tert-butyldiphenylsiloxy)-3,5-isopropylidenedioxy-2,4-dimethylpentane