(3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene

Base Information

• Chemical Name: (3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene
• CAS No.: 132409-22-4
• Molecular Formula: C₁₃H₁₄Br₂O₂
• Molecular Weight: 362.061
• Mol file: 132409-22-4.mol

Synonyms:(3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene

Chemical Property of (3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene

There total 2 articles about (3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene 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:

[(2S,3R)-3-[(benzyloxy)methyl]-2-methyloxiran-2-yl]methanol (115936-20-4,794513-02-3) → (3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene (132409-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1. oxalyl chloride, dimethyl sulfoxide, 2. triethylamine / 1. CH₂Cl₂, -78 deg C, 1.5h, 2. -78 deg C to 0 deg C

2: 1. triphenylphosphine, triethylamine / 1. CH₂Cl₂, r.t.; 2. CH₂Cl₂, -78 deg C to 0 deg C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; triphenylphosphine;

DOI:10.1021/jo00006a049

Reference yield:

carbon tetrabromide (558-13-4) + (2S,3R)-3-Benzyloxymethyl-2-methyl-oxirane-2-carbaldehyde (115827-28-6,118574-89-3) → (3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene (132409-22-4)

Guidance literature:

With triethylamine; triphenylphosphine; Yield given. Multistep reaction; 1. CH₂Cl₂, r.t.; 2. CH₂Cl₂, -78 deg C to 0 deg C;

DOI:10.1021/jo00006a049

Reference yield: 94.0%

(3S,4R)-5-(Benzyloxy)-1,1-dibromo-3,4-epoxy-3-methyl-1-pentene (132409-22-4) → (3S,4R)-5-(Benzyloxy)-1-bromo-3,4-epoxy-3-methyl-1-pentyne (132409-23-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo00006a049

upstream raw materials:

carbon tetrabromide

(2S,3R)-3-Benzyloxymethyl-2-methyl-oxirane-2-carbaldehyde

[(2S,3R)-3-[(benzyloxy)methyl]-2-methyloxiran-2-yl]methanol

Downstream raw materials:

(3S,4R)-5-(Benzyloxy)-1-bromo-3,4-epoxy-3-methyl-1-pentyne

(2S,3R)-3-Benzyloxymethyl-2-ethynyl-2-methyl-oxirane

(R)-2-Benzyloxy-1-((R)-2,5-dimethyl-2,5-dihydro-furan-2-yl)-ethanol

4-((2S,3R)-3-Benzyloxymethyl-2-methyl-oxiranyl)-but-3-yn-2-ol