Butanoic acid, 3-hydroxy-4-(phenylmethoxy)-, methyl ester, (3R)-

Base Information

• Chemical Name: Butanoic acid, 3-hydroxy-4-(phenylmethoxy)-, methyl ester, (3R)-
• CAS No.: 114784-19-9
• Molecular Formula: C12H16O4
• Molecular Weight: 224.257
• Mol file: 114784-19-9.mol

Synonyms:

Chemical Property of Butanoic acid, 3-hydroxy-4-(phenylmethoxy)-, methyl ester, (3R)-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Butanoic acid, 3-hydroxy-4-(phenylmethoxy)-, methyl ester, (3R)-

There total 7 articles about Butanoic acid, 3-hydroxy-4-(phenylmethoxy)-, methyl 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: 91.0%

methanol (67-56-1) + tert-Butyl (S)-4-benzyloxy-3-hydroxybutanoate (147849-59-0) → (R)-Methyl 4-benzyloxy-3-hydroxybutanoate (114784-19-9) + Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate (147849-60-3)

Guidance literature:

With sulfuric acid; Title compound not separated from byproducts; Heating;

DOI:10.1016/S0040-4020(01)86300-6

Reference yield: 70.0%

benzyl bromide (100-39-0) + (R)-methyl 3,4-dihydroxybutanoate (114819-45-3) → (R)-Methyl 4-benzyloxy-3-hydroxybutanoate (114784-19-9) + (R)-4-benzyloxy-dihydro-2(3H)-furanone (114784-20-2)

Guidance literature:

With silver(l) oxide; In tetrahydrofuran; at 10 ℃; for 0.5h; Product distribution; The reaction was performed under sonication. Other conditions, no sonication or using other bases, decreased the yield of the monobenzylation at the primary hydroxyl group.;

DOI:10.1016/S0040-4039(01)83850-8

Reference yield:

C3H5O2(1-)*Br(1-)*Zn(2+) + benzyloxyacetoaldehyde (60656-87-3) → (R)-Methyl 4-benzyloxy-3-hydroxybutanoate (114784-19-9) + Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate (147849-60-3)

Guidance literature:

With (-)-N,N-dimethylaminoisoborneol; diethylzinc; In tetrahydrofuran; at -20 - 0 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1021/ol0531381

upstream raw materials:

methanol

tert-Butyl (S)-4-benzyloxy-3-hydroxybutanoate

benzyl bromide

(R)-methyl 3,4-dihydroxybutanoate

Downstream raw materials:

tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate

(4R,6R)-6-Benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-one

(4R,6S)-6-(benzyloxy)methyl-4-hydroxy-tetrahydro-2-pyrone