methyl (3S)-5-bromo-3-methylpentanoate

Base Information

• Chemical Name: methyl (3S)-5-bromo-3-methylpentanoate
• CAS No.: 80654-39-3
• Molecular Formula: C7H13BrO2
• Molecular Weight: 209.08100
• DSSTox Substance ID: DTXSID80840320
• Mol file: 80654-39-3.mol

Synonyms:80654-39-3;Pentanoic acid, 5-bromo-3-methyl-, methyl ester, (S)-;methyl (3S)-5-bromo-3-methylpentanoate;DTXSID80840320;(S)-5-Bromo-3-methylpentanoic acid methyl ester

Chemical Property of methyl (3S)-5-bromo-3-methylpentanoate

Chemical Property:

• PSA: 26.30000
• LogP: 1.97060
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 208.00989
• Heavy Atom Count: 10
• Complexity: 104

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCBr)CC(=O)OC
• Isomeric SMILES: C[C@H](CCBr)CC(=O)OC

Technology Process of methyl (3S)-5-bromo-3-methylpentanoate

There total 2 articles about methyl (3S)-5-bromo-3-methylpentanoate 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: 95.7%

methyl 3-(R)-methyl-5-hydroxypentanoate (32365-96-1,68702-74-9,86462-82-0) → methyl (R)-(+)-5-bromo-3-methylpentanoate (80654-39-3)

Guidance literature:

With hydrogen bromide; In methanol; 1.) 0 deg C, 5 min, 2.) r.t., 90 min;

DOI:10.1002/hlca.19840670132

Reference yield:

(4R)-5-methoxycarbonyl-4-methylvaleric acid (71685-51-3) → methyl (R)-(+)-5-bromo-3-methylpentanoate (80654-39-3)

Guidance literature:

With bromine; silver(l) oxide; Yield given. Multistep reaction; 1.) H₂O, 40 deg C, 4.5 h, 2.) CCl₄, 1.5 h;

Reference yield:

methyl (R)-(+)-5-bromo-3-methylpentanoate (80654-39-3) → methyl (2RS,4R,8R)-10 bromo-8-methyl-4-(1,3,6-trioxaheptyl)decanoate

Guidance literature:

Multi-step reaction with 8 steps

1: 93.5 percent / DIBAH in hexan / tetrahydrofuran / 1.) 4.5 h, at 0 deg C, 2.) 30 min. at r.t.

2: 88 percent / 20 h / 0 - 20 °C

3: 96 percent / 1.) Mg, I₂, 3.) CuI / tetrahydrofuran / 1.) 5 min, 2.) reflux 30 min, , 10 min, in THF, 3.) 1 h, -30 deg C, 4 h, O deg C, 14 h, r.t.,

4: 84 percent / 1.) diisopropylethylamine, 2.) PPTS / 1.) 3 h, r.t., CH₂Cl₂, 2.) 2 h r.t., CH₂Cl₂/MeOH 1:1

5: 69 percent / 1.) NaIO₄, RuCl₃ / 1.) CCl₄, CH₃Cn, H₂O, at 0 deg C, 3.5 h, 2.) in ether,

6: 68 percent / 1.) cyclohexylisopropylamine, BuLi in hexan, 2.) HMPT / tetrahydrofuran / 1.) 10 min, 10 min, 2.) -78 deg C, 30 min 3.) -30 deg C, 30 min, 1 h r.t.,

7: 73 percent / PPTS / methanol / 72 h / Ambient temperature

8: 68 percent / CBr₄, pyridine, Ph₃P / diethyl ether / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; sodium periodate; copper(l) iodide; n-butyllithium; carbon tetrabromide; N-cyclohexylisopropylamine; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; magnesium; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1002/hlca.19840670132

upstream raw materials:

(4R)-5-methoxycarbonyl-4-methylvaleric acid

methyl 3-(R)-methyl-5-hydroxypentanoate

Downstream raw materials:

methyl (R)-3-methyl-5-o-nitrophenylselenopentanoate

(4R,8R)-1-<(4-methoxyphenyl)diphenylmethoxy>-8-methy-10-(tetrahydropyranyloxy)-4-decanol

Refernces

• 1、 Masuda, Satoru,Kuwahara, Shigefumi,Suguro, Toshio,Mori, Kenji. "Stereoselective Synthesis of (S,E)-6-Isopropyl-3,9-dimethyl-5,8-decadienyl Acetate, the (S)-Enantiomer of the Yellow Scale Pheromone". . p. 2515 - 2520. Retrieved 2007/10/02.