Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester

Base Information

• Chemical Name: Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester
• CAS No.: 185628-39-1
• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.358
• Mol file: 185628-39-1.mol

Synonyms:Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester

Chemical Property of Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester

There total 4 articles about Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester 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:

phenylglyoxal hydrate (1074-12-0) → Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester (185628-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min; 0 deg C, 1 h, 2.) CH₂Cl₂, -5 deg C, 0.5 h

2: LiBH₄ / tetrahydrofuran / 1 h / Ambient temperature

3: pyridine, DMAP / 1 h / Ambient temperature

With pyridine; dmap; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran;

DOI:10.1016/0040-4020(95)00858-6

Reference yield:

(2'S,3'S,4S)-3-(3'-hydroxy-2'-methyl-4'-oxo-4'-phenylbutyryl)-4-isopropyl-2-oxazolidinone (155324-36-0) → Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester (185628-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: LiBH₄ / tetrahydrofuran / 1 h / Ambient temperature

2: pyridine, DMAP / 1 h / Ambient temperature

With pyridine; dmap; lithium borohydride; In tetrahydrofuran;

DOI:10.1016/0040-4020(95)00858-6

Reference yield:

(2S,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-2-methyl-4-phenyl-butane-1,4-dione (156426-86-7) → Acetic acid (2S,3R)-2,4-diacetoxy-3-methyl-1-phenyl-butyl ester (185628-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / 18 h / Ambient temperature

2: pyridine, 4-dimethylaminopyridine / 18 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1248/cpb.44.2003

upstream raw materials:

(2S,3S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-4-phenyl-butane-1,4-dione

phenylglyoxal hydrate

(2'S,3'S,4S)-3-(3'-hydroxy-2'-methyl-4'-oxo-4'-phenylbutyryl)-4-isopropyl-2-oxazolidinone

Downstream raw materials:

(2R,3R)-2-methyl-4-phenylbutane-1,3-diyl diacetate