(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

Base Information

• Chemical Name: (E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate
• CAS No.: 155430-43-6
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359
• Mol file: 155430-43-6.mol

Synonyms:(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

Chemical Property of (E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

There total 7 articles about (E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate 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:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde (618096-09-6) → (E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate (155430-43-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; Yield given; 1.) 0 deg C; 2.) -78 deg C;

DOI:10.1016/S0040-4039(00)73733-6

Reference yield:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol (73814-75-2,73814-80-9,73837-43-1,79027-31-9,81520-04-9,81520-05-0,81520-09-4,104320-78-7,115458-81-6,115458-82-7,125873-79-2,125873-80-5,81520-08-3) → (E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate (155430-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 17.4 g / tetrahydrofuran / 0.5 h / 0 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 2.2: Wadsworth-Horner-Emmons reaction;

DOI:10.1021/ol035227o

Reference yield:

(2S)-3-(benzyloxy)-2-methylpropanal (79027-28-4) → (E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate (155430-43-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

1.2: 22.7 g / tetrahydrofuran / 0.5 h / -78 °C

2.1: DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

3.1: 15 g / mCPBA / CH₂Cl₂ / 0.5 h / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

5.2: 17.4 g / tetrahydrofuran / 0.5 h / 0 °C

With oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; 1.2: Horner-Emmons reaction / 4.1: Swern oxidation / 5.2: Wadsworth-Horner-Emmons reaction;

DOI:10.1021/ol035227o

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol

(R)-3-(benzyloxy)-2-methylpropan-1-ol

Downstream raw materials:

(E)-(4S,5R,6S)-ethyl 7-benzyloxy-5-hydroxy-4,6-dimethyl-2-heptenoate

2,2-Dimethyl-propionic acid (3S,4R,5R,6S,7R,8R,9S,10S)-11-benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-5,7,9-tris-triethylsilanyloxy-undecyl ester

[(2R,3R)-3-((1R,2R,3S,4R,5R,6S,7S)-8-Benzyloxy-1,3,5,7-tetramethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

(E)-3-[(2S,3S)-3-((1S,2S,3R,4S,5S)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester