(3S,6S,SS,1'R,3'S)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene

Base Information

• Chemical Name: (3S,6S,SS,1'R,3'S)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene
• CAS No.: 114882-96-1
• Molecular Formula: C₂₁H₂₈O₂S
• Molecular Weight: 344.518
• Mol file: 114882-96-1.mol

Synonyms:(3S,6S,SS,1'R,3'S)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene

Chemical Property of (3S,6S,SS,1'R,3'S)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6S,SS,1'R,3'S)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene

There total 18 articles about (3S,6S,SS,1'R,3'S)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene 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:

(3S,6S,SR,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-66-8,114790-86-2) → (3S,6S,SS,1'R,3'R)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-51-1,114882-96-1,114883-11-3,114883-12-4)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -10 ℃; for 1h; Yield given;

DOI:10.1021/ja00222a036

Reference yield:

(3S,6S,SS,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-66-8) → (3S,6S,SS,1'R,3'R)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-51-1) + (3S,6S,SS,1'R,3'S)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene (114882-96-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -10 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00222a036

Reference yield:

3-Methyl-2-cyclopenten-1-one (2758-18-1) → (3S,6S,SS,1'R,3'R)-3,6-dimethyl-3-(3-hydroxy-1-methyl-2-methylenecyclopentyl)-1-(phenylsulfinyl)cyclohexene (114790-51-1,114882-96-1,114883-11-3,114883-12-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Br₂/Et₃N, 2.) p-toluenesulfonic acid / 1.) CCl₄, 2.) benzene, reflux

2: 1.) n-BuLi, 3.) oxalic acid / 1.) THF, hexane, -78 deg C, 45 min; 2.) THF, hexane, -78 deg C, 30 min, 25 deg C, 15 min; 3.) CH₂Cl₂-water, 25 deg C, 12 h

3: 1.) LDA / 1.) THF, -78 deg C, 10 min; 2.) THF, -78 deg C, 15 min

4: LiBH₄ / 1.) THF,0 deg C, 2.) 25 deg C, 18 h

5: triethylamine / acetonitrile / 2 h / -10 °C

6: 3A molecular sieves, PCC / CH₂Cl₂ / 3 h / 25 °C

7: DBN / toluene / 1.5 h / 80 °C

8: CeCl_3.7H₂O, sodium borohydride / methanol / 1 h / -10 °C

With sodium tetrahydroborate; lithium borohydride; n-butyllithium; cerium(III) chloride; 2,6-dichloro-benzonitrile; 3 A molecular sieve; bromine; oxalic acid; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00222a036

upstream raw materials:

(3S,6S,SR,1'S)-3,6-dimethyl-3-(1-methyl-2-methylene-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene

3-Methyl-2-cyclopenten-1-one

2-(methoxycarbonyl)-3-methyl-2-cyclopenten-1-one

6-bromo-7-methyl-1,4-dioxaspiro<4.4>non-6-ene

Downstream raw materials:

(9S,10S,SR)-12,13-deoxy-9,10-dihydro-10-(phenylsulfinyl)trichothecene

(9S,10R,SR)-12,13-deoxy-9,10-dihydro-10-(phenylsulfinyl)trichothecene

(9S,10S,SS)-12,13-deoxy-9,10-dihydro-10-(phenylsulfinyl)trichothecene

(9S,10R,SS)-12,13-deoxy-9,10-dihydro-10-(phenylsulfinyl)trichothecene