(3alpha,5R,6beta,22E)-6-Methoxy-3,5-cyclostigmast-22-ene

Base Information

• Chemical Name: (3alpha,5R,6beta,22E)-6-Methoxy-3,5-cyclostigmast-22-ene
• CAS No.: 53603-94-4
• Molecular Formula: C30H50O
• Molecular Weight: 426.726
• European Community (EC) Number: 611-021-5
• DSSTox Substance ID: DTXSID401232220
• Nikkaji Number: J1.299.275K
• Mol file: 53603-94-4.mol

Synonyms:53603-94-4;DTXSID401232220;10.14272/AQOBCZGNYIDKIJ-CEXMQFLDSA-N.1;10.14272/AQOBCZGNYIDKIJ-CEXMQFLDSA-N.2;doi:10.14272/AQOBCZGNYIDKIJ-CEXMQFLDSA-N.1;doi:10.14272/AQOBCZGNYIDKIJ-CEXMQFLDSA-N.2;(3alpha,5R,6beta,22E)-6-Methoxy-3,5-cyclostigmast-22-ene

Chemical Property of (3alpha,5R,6beta,22E)-6-Methoxy-3,5-cyclostigmast-22-ene

Chemical Property:

• Melting Point: 55-56 °C
• Boiling Point: 484.5±14.0 °C(Predicted)
• PSA: 9.23000
• Density: 0.98±0.1 g/cm3(Predicted)
• LogP: 8.14470
• Solubility.: Ethyl Acetate, Methyl Chloride
• XLogP3: 9.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 709

Purity/Quality:

(3β,5α,6β,22E)-3,5-Cyclostigmast-22-ene6-MethylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C=CC(C)C1CCC2C1(CCC3C2CC(C45C3(CCC4C5)C)OC)C)C(C)C
• Isomeric SMILES: CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@H]([C@@]45[C@@]3(CC[C@@H]4C5)C)OC)C)C(C)C
• Uses: (3β,5α,6β,22E)-3,5-Cyclostigmast-22-ene 6-Methyl Ether is an intermediate in the preparation of β-Sitosterol (S497050), a common plant sterol.

Technology Process of (3alpha,5R,6beta,22E)-6-Methoxy-3,5-cyclostigmast-22-ene

There total 27 articles about (3alpha,5R,6beta,22E)-6-Methoxy-3,5-cyclostigmast-22-ene 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: 98.0%

methanol (67-56-1) + stigmasteryl tosylate (53139-42-7) → stigmasterol methyl ether (53603-94-4)

Guidance literature:

With potassium acetate; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/ol102936z

Reference yield: 71.0%

Stigmasterol (83-48-7) → stigmasterol methyl ether (53603-94-4)

Guidance literature:

Stigmasterol; With pyridine; p-toluenesulfonyl chloride; at 0 ℃; for 21h;

With methanol; at 75 ℃; for 3h;

DOI:10.1039/d1ob02150h

Reference yield: 60.0%

methanol (67-56-1) + stigmasteryl tosylate (53139-42-7) → iso-stigmasteryl methyl ether (10453-25-5) + stigmasterol methyl ether (53603-94-4)

Guidance literature:

With pyridine; for 6h; Reflux;

DOI:10.1021/jf9024745

upstream raw materials:

methanol

stigmasteryl tosylate

potassium acetate

(E)-(3S,6R)-3-Isopropyl-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-hept-4-en-1-ol

Downstream raw materials:

β-sitosterol

6β-methoxy-3α,5β-cyclo-23-norchol-22-al

(S)-2-ethyl-3-methylbutanal

3α,5α-cyclo-stigmasta-6,22t-diene

Refernces

• 1、 Fall, Yagamare,Gómez, Generosa,López, Carlos Silva,Nieto Faza, Olalla,Santalla, Hugo. "On the mechanism of the dyotropic expansion of hydrindanes into decalins". supporting information. p. 1073 - 1079. Retrieved 2022/02/16.
• 2、 Seck, Insa,Fall, Alioune,Lago, Carmen,Sène, Massène,Gaye, Mohamed,Seck, Matar,Gómez, Generosa,Fall, Yagamare. "Synthesis of a Cholesterol Side-Chain Triazole Analogue via 'Click' Chemistry". . p. 2826 - 2830. Retrieved 2015/09/15.