1-Cyclohexene-1-carboxylicacid, 4-[(1S,3S)-3-hydroxy-1,5-dimethylhexyl]-, methyl ester, (4R)-

Base Information

• Chemical Name: 1-Cyclohexene-1-carboxylicacid, 4-[(1S,3S)-3-hydroxy-1,5-dimethylhexyl]-, methyl ester, (4R)-
• CAS No.: 64314-14-3
• Molecular Formula: C16H28 O3
• Molecular Weight: 268.39172
• Mol file: 64314-14-3.mol

Synonyms:1-Cyclohexene-1-carboxylicacid, 4-(3-hydroxy-1,5-dimethylhexyl)-, methyl ester, [4R-[4R*(1S*,3S*)]]-;(+)-Epijuvabiol; (4R,1'S,3'S)-Epijuvabiol; Epijuvabiol

Chemical Property of 1-Cyclohexene-1-carboxylicacid, 4-[(1S,3S)-3-hydroxy-1,5-dimethylhexyl]-, methyl ester, (4R)-

Chemical Property:

• PSA: 46.53000
• LogP: 3.31910

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Cyclohexene-1-carboxylicacid, 4-[(1S,3S)-3-hydroxy-1,5-dimethylhexyl]-, methyl ester, (4R)-

There total 27 articles about 1-Cyclohexene-1-carboxylicacid, 4-[(1S,3S)-3-hydroxy-1,5-dimethylhexyl]-, methyl ester, (4R)- 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,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-cyclohex-1-enecarboxylic acid methyl ester (80373-80-4) → Epijuvabiol (64314-14-3)

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-[(1S,3S)-1-isobutyl-3-((R)-4-methyl-cyclohex-3-enyl)-butoxy]-diphenyl-silane → Epijuvabiol (64314-14-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

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

3: 30 percent / lithium diethylamide / diethyl ether

4: 65 percent / PBr₃ / tetrahydrofuran / 0 °C

5: 88 percent / 2-nitropropane, KOH / H₂O; tetrahydrofuran; propan-2-ol / 1 h / 40 - 50 °C

6: 87 percent / manganese dioxide / acetic acid / 12 h / 22 °C

7: 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; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; isopropyl alcohol; benzene;

DOI:10.1021/jo00339a054

upstream raw materials:

(+)-epijuvabione

(R)-4-[(1S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-cyclohex-1-enecarboxylic acid methyl ester

(R)-4-[(1S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-cyclohex-1-enecarbaldehyde

[(1S,3S)-3-((R)-4-Bromomethyl-cyclohex-3-enyl)-1-isobutyl-butoxy]-tert-butyl-diphenyl-silane

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