Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester
• CAS No.: 143520-72-3
• Molecular Formula: C₃₄H₄₈O₄S
• Molecular Weight: 552.819

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

There total 8 articles about Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 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:

ergosterol acetate (1108-03-8,2874-25-1,3957-39-9,57760-54-0,60018-28-2,78148-63-7,125225-12-9,2418-45-3) → Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (143520-72-3)

Guidance literature:

Multi-step reaction with 8 steps

1: CHCl₃ / 1 h / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.5 h

3: 1.) n-BuLi / 1.) THF, -70 deg C, 30 min

4: 5percent Na/Hg, NaH₂PO₄ / methanol / 15 h / 0 °C

5: LiAlH₄ / tetrahydrofuran / 3 h / Heating

6: PPTS / ethanol

7: diethyl ether; benzene / 2.5 h / Ambient temperature; Irradiation

8: pyridine / 1.) 5 deg C, 24 h, 2.) EtOH, heating, 8 h

With pyridine; sodium dihydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; pyridinium p-toluenesulfonate; ozone; In tetrahydrofuran; methanol; diethyl ether; ethanol; chloroform; benzene;

DOI:10.1016/0040-4039(92)80013-A

Reference yield:

cholesta-5,7,22-triene-3β,25-diol (66513-97-1) → Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (143520-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; benzene / 2.5 h / Ambient temperature; Irradiation

2: pyridine / 1.) 5 deg C, 24 h, 2.) EtOH, heating, 8 h

With pyridine; In diethyl ether; benzene;

DOI:10.1016/0040-4039(92)80013-A

Reference yield:

(3S,9S,10R,13R,14R,17R)-17-[(E)-(R)-1,5-Dimethyl-5-(tetrahydro-pyran-2-yloxy)-hex-2-enyl]-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol → Toluene-4-sulfonic acid (S)-3-[2-[(1R,3aS,7aR)-1-((E)-(R)-5-hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (143520-72-3)

Guidance literature:

Multi-step reaction with 3 steps

1: PPTS / ethanol

2: diethyl ether; benzene / 2.5 h / Ambient temperature; Irradiation

3: pyridine / 1.) 5 deg C, 24 h, 2.) EtOH, heating, 8 h

With pyridine; pyridinium p-toluenesulfonate; In diethyl ether; ethanol; benzene;

DOI:10.1016/0040-4039(92)80013-A

upstream raw materials:

25-hydroxy-28-norvitamin D₂

p-toluenesulfonyl chloride

ergosterol acetate

cholesta-5,7,22-triene-3β,25-diol

Downstream raw materials:

5,6-cis- and 5,6-trans-1α,25-dihydroxy-28-norvitamin D₂

1α,25-dihydroxy-28-norvitamin D₂

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