3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien

Base Information

• Chemical Name: 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien
• CAS No.: 87080-74-8
• Molecular Formula: C₃₅H₅₄O₄SSi
• Molecular Weight: 598.963
• Mol file: 87080-74-8.mol

Synonyms:3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien

Chemical Property of 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien

There total 25 articles about 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien 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: 95.0%

3β-((tert-butyldimethylsilyl)oxy)-22-hydroxy-23,24-bisn-orchol-5,7-diene (87080-73-7) + p-toluenesulfonyl chloride (98-59-9) → 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien (87080-74-8)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1016/j.steroids.2017.05.013

Reference yield:

3β-tert-Butyldimethylsilyloxy-ergosta-5,7,22-triene (95307-26-9) → 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien (87080-74-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / Pb(OAc)4 / CH₂Cl₂; acetic acid / 1 h / -5 - 0 °C

2: O₃; O₂; pyridine / CH₂Cl₂ / 0.58 h / -60 °C

3: NaBH₄ / CH₂Cl₂; methanol / 12 h / -50 - 0 °C

4: 88 percent / lithium naphthalenide / tetrahydrofuran / 1.5 h / 0 °C

5: 86 percent / pyridine / 4 h / -5 °C

With pyridine; lead(IV) acetate; sodium tetrahydroborate; oxygen; ozone; naphthalen-1-yl-lithium; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1: Addition / 2: Oxidation / 3: Reduction / 4: deprotection / 5: Tosylation;

DOI:10.1055/s-1999-3547

Reference yield:

3β-tert-butyldimethylsilyloxy-5α,8α-(1,4-dioxo-1,2,3,4-tetrahydro-phthalazine-2,3-diyl)-23,24-bisnorchol-6-en-22-al → 3β-((tert-butyldimethylsilyl)oxy)-22-tosyloxy-23,24-bisn-orchol-5,7-dien (87080-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / CH₂Cl₂; methanol / 12 h / -50 - 0 °C

2: 88 percent / lithium naphthalenide / tetrahydrofuran / 1.5 h / 0 °C

3: 86 percent / pyridine / 4 h / -5 °C

With pyridine; sodium tetrahydroborate; naphthalen-1-yl-lithium; In tetrahydrofuran; methanol; dichloromethane; 1: Reduction / 2: deprotection / 3: Tosylation;

DOI:10.1055/s-1999-3547

upstream raw materials:

3β-((tert-butyldimethylsilyl)oxy)-22-hydroxy-23,24-bisn-orchol-5,7-diene

p-toluenesulfonyl chloride

Ergosterol

tert-butyldimethylsilyl chloride

Downstream raw materials:

cholesta-5,7,24-triene-3β-ol

calcidiol