(23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene

Base Information

• Chemical Name: (23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene
• CAS No.: 267410-57-1
• Molecular Formula: C₃₅H₅₁BrO₄S
• Molecular Weight: 647.758
• Mol file: 267410-57-1.mol

Synonyms:(23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene

Chemical Property of (23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene

There total 6 articles about (23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + (23Z)-24-bromo-6β-methoxy-3α,5-cyclo-5α-cholest-23-en-21-ol (267410-50-4) → (23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene (267410-57-1)

Guidance literature:

With pyridine; In dichloromethane; for 24h;

DOI:10.1002/(sici)1099-0690(200003)2000:6<1027::aid-ejoc1027>3.0.co;2-e

Reference yield:

4-methyl-2-pentyn-1-ol (15787-92-5) → (23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene (267410-57-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Red-Al / toluene; diethyl ether / 4 h / 20 °C

1.2: 77 percent / bromine; pyridine / toluene; CH₂Cl₂; diethyl ether / 0.33 h / -78 °C

2.1: 85 percent / PBr₃; pyridine / diethyl ether / 0.33 h / 4 °C

3.1: 80 percent / LDA; n-BuLi / tetrahydrofuran / 3.5 h / -78 °C

4.1: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -30 - -20 °C

5.1: 95 percent / pyridine / CH₂Cl₂ / 24 h

With pyridine; n-butyllithium; phosphorus tribromide; diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1.1: Reduction / 1.2: Bromination / 2.1: Substitution / 3.1: Alkylation / 4.1: Reduction / 5.1: Esterification;

DOI:10.1002/(sici)1099-0690(200003)2000:6<1027::aid-ejoc1027>3.0.co;2-e

Reference yield:

(Z)-1,3-dibromo-4-methylpent-2-ene (140837-49-6) → (23Z)-24-bromo-6β-methoxy-21-tosyloxy-3α,5-cyclo-5α-cholest-23-ene (267410-57-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / LDA; n-BuLi / tetrahydrofuran / 3.5 h / -78 °C

2: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -30 - -20 °C

3: 95 percent / pyridine / CH₂Cl₂ / 24 h

With pyridine; n-butyllithium; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1: Alkylation / 2: Reduction / 3: Esterification;

DOI:10.1002/(sici)1099-0690(200003)2000:6<1027::aid-ejoc1027>3.0.co;2-e

upstream raw materials:

p-toluenesulfonyl chloride

(23Z)-24-bromo-6β-methoxy-3α,5-cyclo-5α-cholest-23-en-21-ol

4-methyl-2-pentyn-1-ol

(Z)-1,3-dibromo-4-methylpent-2-ene