(20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE

Base Information

• Chemical Name: (20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE
• CAS No.: 51231-24-4
• Molecular Formula: C30H44O4S
• Molecular Weight: 500.743
• Mol file: 51231-24-4.mol

Synonyms:(20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE

Chemical Property of (20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE

Chemical Property:

• PSA: 60.98000
• LogP: 7.70100

Purity/Quality:

99% ^*data from raw suppliers

(3α,5R,6β,20S)-6-Methoxy-3,5-cyclopregnane-30-methanol4-Methylbenzenesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3α,5R,6β,20S)-6-Methoxy-3,5-cyclopregnane-30-methanol 4-Methylbenzenesulfonate is a tosylated derivative that have been utilized in the biosynthetic studies of cholic acids and vitamin D3 derivatives.

Technology Process of (20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE

There total 13 articles about (20S)-6-METHOXY-20-(P-TOLUENESULFONOXY-METHYL)-3B,5-CYCLO-5A-PREGNANE 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: 91.0%

p-toluenesulfonyl chloride (98-59-9) + (20R)-22-Hydroxy-6β-methoxy-3α,5-cyclo-23,24-dinor-5α-cholane → 6β-methoxy-(20S)-methyl-3α,5-cyclo-5α-pregnan-21-ol p-toluenesulfonate (51231-24-4)

Guidance literature:

With pyridine;

Reference yield: 90.0%

3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether (51231-23-3) + p-toluenesulfonyl chloride (98-59-9) → (20S)-(6β-Methoxy-20-methyl-3α,5-cyclo-5α-pregnan-21-ol)-p-toluolsulfonat (51231-24-4)

Guidance literature:

With pyridine; dmap; at 0 ℃; for 5h;

Reference yield:

stigmasterol methyl ether (53603-94-4) → (20S)-(6β-Methoxy-20-methyl-3α,5-cyclo-5α-pregnan-21-ol)-p-toluolsulfonat (51231-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone / CH₂Cl₂; methanol / 12 h / -78 °C

1.2: 69 percent / NaBH₄ / CH₂Cl₂; methanol; aq. ethanol / 20 °C

2.1: pyridine

With pyridine; ozone; In methanol; dichloromethane; 1.1: Oxidation / 1.2: Reduction / 2.1: Tosylation;

DOI:10.1021/jo991370c

upstream raw materials:

p-toluenesulfonyl chloride

6β-Methoxy-3α,5-cyclo-23,24-dinor-5α-cholan-22-al

3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carboxylic acid

Downstream raw materials:

6β-methoxy-3α,5-cyclo-5α-24-norcholan-23-ol 23-tosylate

(25R)-6β-methoxy-24-phenylsulfonyl-3α,5-cyclo-5α-cholestan-26-ol 26-(2'-tetrahydropyranyl) ether

25-hydroxychlolesterol

26,27-dinorcholest-5-en-23-yn-3β-ol