(E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester
• CAS No.: 212509-17-6
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 212509-17-6.mol

Synonyms:(E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester

Chemical Property of (E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester

There total 3 articles about (E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl 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:

(E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol (121352-87-2) → (E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester (212509-17-6)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.) -40 deg C, 8 h, 2.) -10 deg C, 8 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, 0 deg C, 1 h

3: NaH / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 0 deg C, 30 min

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a802947d

Reference yield:

((2S,3S)-3-(1-(benzyloxy)-2-methylpropan-2-yl)oxiran-2-yl)methanol (130199-57-4) → (E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester (212509-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, 0 deg C, 1 h

2: NaH / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 0 deg C, 30 min

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1039/a802947d

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (2R,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane-2-carbaldehyde → (E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester (212509-17-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) 0 deg C, 1 h, 2.) 0 deg C, 30 min;

DOI:10.1039/a802947d

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol

((2S,3S)-3-(1-(benzyloxy)-2-methylpropan-2-yl)oxiran-2-yl)methanol

Downstream raw materials:

epothilone B

(4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione

epothilone D

(2S,3R)-5-Benzyloxy-2,4,4-trimethyl-3-triethylsilanyloxy-pentanal