methyl (2RS,3SR)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate

Base Information

• Chemical Name: methyl (2RS,3SR)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate
• CAS No.: 92817-35-1
• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.354
• Mol file: 92817-35-1.mol

Synonyms:methyl (2RS,3SR)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate

Chemical Property of methyl (2RS,3SR)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (2RS,3SR)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate

There total 4 articles about methyl (2RS,3SR)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate 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:

2-benzyloxypropionic acid methyl ester (53346-03-5) + benzaldehyde (100-52-7) → methyl (2RS,3SR)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate (92817-35-1) + methyl (2RS,3RS)-2-methyl-2-(benzyloxy)-3-hydroxylbenzenepropanoate (92844-11-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 0.0166667h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00338a027

Reference yield:

benzaldehyde (100-52-7) + ((E)-2-Benzyloxy-1-methoxy-propenyloxy)-trimethyl-silane (221280-76-8) → (2R,3R)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid methyl ester (152982-18-8) + (2R,3S)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid methyl ester (71699-57-5,71699-58-6,92817-35-1,92844-11-6) + (2S,3R)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid methyl ester (152982-17-7)

Guidance literature:

With tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-<(N-naphthylamino)methyl>pyrrolidine; dibutyltin diacetate; In dichloromethane; at -78 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.3987/COM-93-S(T)138

Reference yield:

2-benzyloxypropionic acid methyl ester (53346-03-5) → (2R,3S)-2-Benzyloxy-3-hydroxy-2-methyl-3-phenyl-propionic acid methyl ester (71699-57-5,71699-58-6,92817-35-1,92844-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT

2: 1.) Sn(OTf)2, Bu₂Sn(OAc)2, (S)-1-methyl-2-<(N-naphthylamino)methyl>pyrrolidine / 1.) CH₂Cl₂, RT, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT, 20 h

With tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-<(N-naphthylamino)methyl>pyrrolidine; dibutyltin diacetate; lithium diisopropyl amide;

DOI:10.1246/cl.1992.373

upstream raw materials:

benzaldehyde

((E)-2-Benzyloxy-1-methoxy-propenyloxy)-trimethyl-silane

2-benzyloxypropionic acid methyl ester