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(+)-Bourgeanic acid

Base Information Edit
  • Chemical Name:(+)-Bourgeanic acid
  • CAS No.:43043-17-0
  • Molecular Formula:C22H42O5
  • Molecular Weight:386.572
  • Hs Code.:
  • Mol file:43043-17-0.mol
(+)-Bourgeanic acid

Synonyms:(2S,3S,4R,6R)-3-hydroxy-2,4,6-trimethyl-octanoic acid (1S,2R,4R)-1-((S)-1-carboxyethyl)-2,4-dimethyl-hexyl ester;(2S,3S,4R,6R)-3-Hydroxy-2,4,6-trimethyl-octanoic acid (1S,2R,4R)-1-((S)-1-carboxy-ethyl)-2,4-dimethyl-hexyl ester;bourgeanic acid;(1S,2R,4R)-1-[(S)-1-carboxyethyl]-2,4-dimethylhexyl (2S,3S,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoate;

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The product has achieved commercial mass production*data from LookChem market partment
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Chemical Property of (+)-Bourgeanic acid Edit
Chemical Property:
  • PSA:83.83000 
  • LogP:4.76050 
Purity/Quality:
Safty Information:
  • Pictogram(s):  
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MSDS Files:

SDS file from LookChem

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Technology Process of (+)-Bourgeanic acid

There total 29 articles about (+)-Bourgeanic acid 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:
Guidance literature:
Multi-step reaction with 12 steps
1: 80 percent / LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 15 min; -10 deg C, 2 h
2: 74 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
3: H2 / Rh(I)(NBD)(DIPHOS-4)(+)*BF4(-)
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 10 min, 2.) CH2Cl2, -78 deg C, 20 min; 0 deg C, 30 min
6: 83 percent / 2,6-lutidine / CH2Cl2 / 4.5 h / Ambient temperature
7: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 2.) reflux, 8 h
8: 97 percent / 1 M aq. NaClO2, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1.) 0 deg C, 15 min, 2.) r.t., 2.5 h
9: 89 percent / 48percent aq. HF / acetonitrile; tetrahydrofuran / 48 h / Ambient temperature
10: 86 percent / benzenesulfonyl chloride, pyridine / 22 h / 0 °C
11: 61 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 10 min, 2.) 0 deg C, 5.5 h
12: 1.) O3, 2.) 30percent aq. H2O2 / 1.) EtOAc, -78 deg C, 2.) glac. AcOH, r.t., 72 h
With pyridine; 2,6-dimethylpyridine; sodium chlorite; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide; hydrogen fluoride; hydrogen; dihydrogen peroxide; ozone; dimethyl sulfoxide; triethylamine; benzenesulfonyl chloride; lithium diisopropyl amide; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF4; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00091a022
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