(+)-isoepijuvabiol

Base Information

• Chemical Name: (+)-isoepijuvabiol
• CAS No.: 80373-62-2
• Molecular Formula: C₁₆H₂₈O₃
• Molecular Weight: 268.397
• Mol file: 80373-62-2.mol

Synonyms:(+)-isoepijuvabiol

Chemical Property of (+)-isoepijuvabiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-isoepijuvabiol

There total 28 articles about (+)-isoepijuvabiol 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: 88.0%

(R)-4-[(1S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-cyclohex-1-enecarboxylic acid methyl ester (80373-81-5) → (+)-isoepijuvabiol (80373-62-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 7h; Heating;

DOI:10.1021/jo00339a054

Reference yield: 48.0%

methyl (1'R,4R)-4-(2'-formyl-1'-methylethyl)cyclohex-1-ene-1-carboxylate (145353-92-0) + isobutylmagnesium bromide (926-62-5) → methyl (4R,1'R,3'RS)-(+)-4-(1',5'-dimethyl-3'-hydroxyhexyl)-1-cyclohexenecarboxylate (58493-52-0,60134-56-7,60497-70-3,64314-14-3,76549-67-2,80373-62-2)

Guidance literature:

In tetrahydrofuran; at -45 ℃; for 3h;

Reference yield:

tert-Butyl-[(1R,3S)-1-isobutyl-3-((R)-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-butoxy]-diphenyl-silane → (+)-isoepijuvabiol (80373-62-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / diethylaluminum 2,2,6,6-tetramethylpiperidide / benzene / 3 h / 0 °C

2: 30 percent / lithium diethylamide / diethyl ether

3: 65 percent / PBr₃ / tetrahydrofuran / 0 °C

4: 88 percent / 2-nitropropane, KOH / H₂O; tetrahydrofuran; propan-2-ol / 1 h / 40 - 50 °C

5: 87 percent / manganese dioxide / acetic acid / 12 h / 22 °C

6: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 7 h / Heating

With manganese(IV) oxide; potassium hydroxide; diethyl(2,2,6,6-tetramethylpiperidino)aluminium; 2-nitropropane; lithium diethylamide; tetrabutyl ammonium fluoride; phosphorus tribromide; In tetrahydrofuran; diethyl ether; water; acetic acid; isopropyl alcohol; benzene;

DOI:10.1021/jo00339a054

upstream raw materials:

(+)-epijuvabione

methyl (1'R,4R)-4-(2'-formyl-1'-methylethyl)cyclohex-1-ene-1-carboxylate

isobutylmagnesium bromide

(+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester

Downstream raw materials:

(+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester

(R)-4-((R)-3-Hydroxy-1,5-dimethyl-hexyl)-cyclohex-1-enecarboxylic acid

4-((R)-1,5-Dimethyl-3-oxo-hexyl)-cyclohexanecarboxylic acid methyl ester

trans-4-<3(S)-hydroxy-1(R),5-dimethylhexyl>cyclohexane-1-carboxylic acid