(2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid

Base Information

• Chemical Name: (2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid
• CAS No.: 363139-55-3
• Molecular Formula: C₂₃H₂₆O₅
• Molecular Weight: 382.456

Synonyms:(2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid

Chemical Property of (2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid

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Technology Process of (2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid

There total 2 articles about (2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid 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: 52.0%

benzyl bromide (100-39-0) + pivalaldehyde (630-19-3) + diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate (363139-46-2) → (2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid (363139-55-3)

Guidance literature:

diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate; With potassium hydroxide; In methanol;

pivalaldehyde; With toluene-4-sulfonic acid; In benzene; Heating;

benzyl bromide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(01)00907-8

Reference yield: 51.0%

benzyl bromide (100-39-0) + (4'S)-2-[2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid → (2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid (363139-55-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -76 ℃; for 5h;

DOI:10.1002/hlca.200290007

Reference yield: 20.0%

(2R,2'S,4'S)-2-[4-benzyl-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid (363139-55-3) → (3S,4S)-3,4-Dibenzyl-tetrahydro-furan-2,3-diol (363139-63-3) + (2S,3aS,6S,6aS)-6,6a-Dibenzyl-2-tert-butyl-tetrahydro-furo[2,3-d][1,3]dioxole + (2S,3aR,6R,6aS)-6,6a-Dibenzyl-2-tert-butyl-dihydro-furo[2,3-d][1,3]dioxol-5-one

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)00907-8

upstream raw materials:

benzyl bromide

pivalaldehyde

diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate

Downstream raw materials:

(3S,4S)-3,4-Dibenzyl-tetrahydro-furan-2,3-diol

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