glabrescol

Base Information

• Chemical Name: glabrescol
• CAS No.: 274687-63-7
• Molecular Formula: C₃₀H₅₂O₇
• Molecular Weight: 524.739
• Mol file: 274687-63-7.mol

Synonyms:glabrescol

Chemical Property of glabrescol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of glabrescol

There total 16 articles about glabrescol 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: 30.0%

(E)-(R)-2-[(2R,5S,2'S,5'R,2''S,5''R)-5''-(1-Hydroxy-1-methyl-ethyl)-2',2''-dimethyl-dodecahydro-[2,2';5',2'']terfuran-5-yl]-6,10-dimethyl-undeca-5,9-dien-2-ol → glabrescol (274687-63-7,172670-58-5)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ja0007657

Reference yield:

(R)-5-{(2R,3R)-3-[2-((2R,3R)-3-{2-[(2R,3R)-3-(2-{(2R,3R)-3-[2-((R)-3,3-Dimethyl-oxiranyl)-ethyl]-3-methyl-oxiranyl}-ethyl)-3-methyl-oxiranyl]-ethyl}-2-methyl-oxiranyl)-ethyl]-2-methyl-oxiranyl}-2-methyl-pentane-2,3-diol → glabrescol (274687-63-7,172670-58-5)

Guidance literature:

With (R)-10-camphorsulfonic acid; Shi's ketone; In toluene; at 0 ℃; for 1h;

DOI:10.1021/ja000842y

Reference yield:

geranyl phenyl sulfide (35162-74-4) → glabrescol (274687-63-7,172670-58-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BuLi; TMEDA / tetrahydrofuran / -78 °C

2.1: Na; isopropanol / tetrahydrofuran / Heating

3.1: 62 percent / Py; DMAP / CH₂Cl₂ / 24 h / 20 °C

4.1: VO(acac)2; TBHP; TFA / CH₂Cl₂ / 0.5 h / 20 °C

4.2: 28 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

5.1: 30 percent / VO(acac)2; TBHP; TFA / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; n-butyllithium; bis(acetylacetonate)oxovanadium; N,N,N,N,-tetramethylethylenediamine; sodium; isopropyl alcohol; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1.1: Ring cleavage / 2.1: desulfanylation / 3.1: Acetylation / 4.1: Oxidation / 4.2: Reduction / 5.1: Oxidation;

DOI:10.1021/ja0007657

upstream raw materials:

geranyl phenyl sulfide

(E)-(R)-2-[(2S,5R)-5-((E)-(S)-1-Hydroxy-1,5,9-trimethyl-deca-4,8-dienyl)-tetrahydro-furan-2-yl]-6,10-dimethyl-undeca-5,9-dien-2-ol

methanesulfonic acid 1,4-bis-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-4-hydroxy-butyl ester

1,4-bis-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-4-trimethylsilanyloxy-butan-1-ol