Butanoic acid, 3-hydroxy-, (1R)-1-methyl-3-oxo-3-(phenylmethoxy)propyl ester, (3R)-

Base Information

• Chemical Name: Butanoic acid, 3-hydroxy-, (1R)-1-methyl-3-oxo-3-(phenylmethoxy)propyl ester, (3R)-
• CAS No.: 101515-40-6
• Molecular Formula: C15H20O5
• Molecular Weight: 280.321
• Mol file: 101515-40-6.mol

Synonyms:

Chemical Property of Butanoic acid, 3-hydroxy-, (1R)-1-methyl-3-oxo-3-(phenylmethoxy)propyl ester, (3R)-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Butanoic acid, 3-hydroxy-, (1R)-1-methyl-3-oxo-3-(phenylmethoxy)propyl ester, (3R)-

There total 4 articles about Butanoic acid, 3-hydroxy-, (1R)-1-methyl-3-oxo-3-(phenylmethoxy)propyl ester, (3R)- 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: 98.0%

(R)-(-)-2-benzyloxycarbonyl-1-methylethyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate (178246-80-5) → (R)-(-)-2-benzyloxycarbonyl-1-methylethyl (R)-(-)-3-hydroxybutyrate (101515-40-6)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1002/hlca.19960790311

Reference yield:

α-benzyl-ω-[(tert-butyl)diphenylsilyloxy]bis[(R)-oxy(3-methyl)-1-oxopropane-1,3-diyl] (178246-79-2) → (R)-(-)-2-benzyloxycarbonyl-1-methylethyl (R)-(-)-3-hydroxybutyrate (101515-40-6)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; at 0 ℃;

DOI:10.1002/1522-2675(20010613)84:6<1821::AID-HLCA1821>3.0.CO;2-C

Reference yield:

benzyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate → (R)-(-)-2-benzyloxycarbonyl-1-methylethyl (R)-(-)-3-hydroxybutyrate (101515-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / dichloromethane / 0.02 h

2.1: N-ethyl-N,N-diisopropylamine; 2,4,6-trichlorobenzoyl-N',N'-dimethyl-4-aminopyridinium chloride / toluene / 0.02 h

2.2: 24 h / 20 °C

3.1: trifluoroacetic acid / dichloromethane / 0.03 h

With 2,4,6-trichlorobenzoyl-N',N'-dimethyl-4-aminopyridinium chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1080/00397911.2014.919659

upstream raw materials:

(R)-(-)-2-benzyloxycarbonyl-1-methylethyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate

α-benzyl-ω-[(tert-butyl)diphenylsilyloxy]bis[(R)-oxy(3-methyl)-1-oxopropane-1,3-diyl]

(R)-3-hydroxybutanoic benzyl ester

Downstream raw materials:

α-benzyl-ω-[(tert-butyl)diphenylsilyloxy]{bis[(R)-oxy(3-methyl-1-oxopropane-1,3-diyl)]bis[(R)-oxy(3-[13C1]methyl-1-oxo[1,2,3-13C3]propane-1,3-diyl)]}

α-Benzyl-ω-[(tert-butyl)diphenylsilyloxy]octa[(R)-oxy(3-methyl-1-oxopropan-1,3-diyl)]

C₄₈H₆₈O₁₇Si

C₃₉H₅₆O₁₇

Refernces

• 1、 Waser, Peter,Rueping, Magnus,Seebach, Dieter,Duchardt, Elke,Schwalbe, Harald. "On the solution structure of PHB: Preparation and NMR analysis of isotopically labeled oligo[(R)-3-hydroxybutanoic acids] (OHBs)". . p. 1821 - 1845. Retrieved 2007/10/03.