(2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane

Base Information

• Chemical Name: (2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane
• CAS No.: 144666-93-3
• Molecular Formula: C₁₇H₂₄O₂
• Molecular Weight: 260.376
• Mol file: 144666-93-3.mol

Synonyms:(2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane

Chemical Property of (2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane

There total 1 articles about (2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane 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:

benzyl bromide (100-39-0) + (2R,3S)-2,3-epoxynerol (62777-72-4) → (2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane (144666-93-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 10 ℃; for 14h;

DOI:10.1016/S0040-4039(00)82450-8

Reference yield: 89.0%

(2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane (144666-93-3) + phenylacetylene (536-74-3) → (2S,3S)-1-benzyloxy-3,7-dimethyl-3-phenylethynyl-oct-6-en-2-ol

Guidance literature:

phenylacetylene; With n-butyllithium; In diethyl ether; hexane; at 0 ℃; for 0.5h;

With trimethylaluminum; In diethyl ether; hexane; toluene; at 0 - 20 ℃;

(2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane; With boron trifluoride diethyl etherate; In diethyl ether; hexane; toluene; at -78 ℃; for 1.5h; Further stages.;

DOI:10.1039/b308204k

Reference yield:

(2S,3R)-3-Benzyloxymethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane (144666-93-3) → (2R,3R)-1-benzyloxy-2-t-butyldimethylsiloxy-3-methoxy-3-methyl-6-heptene (122804-38-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Dowex 50 (H+) / Ambient temperature

2: 1) O₃, 2) Ph₃P / 1) MeOH, CH₂Cl₂, ca. -60 deg C, 2) up to r.t., then 1 h

3: 1) t-BuOK / 1) THF, 0 deg C, 2) THF, r.t., 3 h

4: 82.3 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

With 1H-imidazole; Dowex 50 (H+); potassium tert-butylate; ozone; triphenylphosphine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88229-6

upstream raw materials:

benzyl bromide

(2R,3S)-2,3-epoxynerol

Downstream raw materials:

(2R,3R)-1-benzyloxy-3-methoxy-3,7-dimethyl-6-octene-2-ol

(2R,3R)-1-benzyloxy-3-methyl-3-methyl-6-heptene-2-ol

(4R,5R)-6-Benzyloxy-5-hydroxy-4-methoxy-4-methyl-hexanal

(2R,3R)-1-benzyloxy-2-t-butyldimethylsiloxy-3-methoxy-3-methyl-6-heptene