(E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate

Base Information

• Chemical Name: (E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate
• CAS No.: 116179-50-1
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359
• Mol file: 116179-50-1.mol

Synonyms:(E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate

Chemical Property of (E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate

There total 2 articles about (E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate 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: 86.0%

(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl benzoate (88218-65-9) → (E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate (116179-50-1)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In decane; dichloromethane; at -20 - 0 ℃; for 18h; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/jacs.5b03229

Reference yield:

(E)-geranyl benzoate (94-48-4) → (E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate (116179-50-1)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) L-(+)-diisopropyl tartrate (L-(+)-DIPT), Ti(OiPr), tert-butyl hydroperoxide (TBHP), 3-Angstroem molecular sieves, 2.) triethanolamine / 1.) CH₂Cl₂, 2,2,4-trimethylpentane, -30 deg C, 3.5 h, 2.) -15 deg C, 0.5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; triethanolamine; L-(+)-diisopropyl tartrate; 3 A molecular sieve;

DOI:10.1021/jo00256a007

Reference yield: 92.0%

benzyl bromide (100-39-0) + (E)-5-((2S,3S)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl benzoate (116179-50-1) → ((2S,3S)-2-methyl-3-((E)-3-methyl-6-phenylhex-3-en-1-yl)oxiran-2-yl)methanol

Guidance literature:

With dilithium tetrachlorocuprate; magnesium; In tetrahydrofuran; diethyl ether; at 0 - 45 ℃; for 2.33333h; Inert atmosphere;

DOI:10.1021/jacs.5b03229

upstream raw materials:

(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl benzoate

(E)-geranyl benzoate

Downstream raw materials:

(-)-6,7-epoxy-8-(benzyloxy)geranyl benzoate

(-)-6,7-epoxy-8-(benzyloxy)geranyl alcohol

(+)-6,7-epoxy-8-(benzyloxy)geranyl chloride

(-)-1-(3-furyl)-7,8-epoxy-9-(benzyloxy)non-3-ene