(7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10⁽¹⁹⁾-choladien-22-yl tosylate

Base Information

• Chemical Name: (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10⁽¹⁹⁾-choladien-22-yl tosylate
• CAS No.: 161003-68-5
• Molecular Formula: C₃₈H₄₆O₆S₃
• Molecular Weight: 694.978
• Mol file: 161003-68-5.mol

Synonyms:(7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10⁽¹⁹⁾-choladien-22-yl tosylate

Chemical Property of (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10⁽¹⁹⁾-choladien-22-yl tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10⁽¹⁹⁾-choladien-22-yl tosylate

There total 5 articles about (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10⁽¹⁹⁾-choladien-22-yl tosylate 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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10(19)-cholien-22-ol (161003-67-4) → (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10(19)-choladien-22-yl tosylate (161003-68-5)

Guidance literature:

With pyridine; at 0 - 5 ℃;

DOI:10.1246/bcsj.67.2494

Reference yield:

(1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclovitamin D2 (161003-63-0) → (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10(19)-choladien-22-yl tosylate (161003-68-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / pyridine / Ambient temperature

2: 1.) O₃, pyridine, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -70 deg C

3: 88 percent / NaBH₄ / CH₂Cl₂; ethanol / 1 h / Ambient temperature

4: 100 percent / pyridine / 0 - 5 °C

With pyridine; sodium tetrahydroborate; dimethylsulfide; ozone; In ethanol; dichloromethane;

DOI:10.1246/bcsj.67.2494

Reference yield:

(7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10(19)-choladien-22-al (161003-73-2) → (7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10(19)-choladien-22-yl tosylate (161003-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaBH₄ / CH₂Cl₂; ethanol / 1 h / Ambient temperature

2: 100 percent / pyridine / 0 - 5 °C

With pyridine; sodium tetrahydroborate; In ethanol; dichloromethane;

DOI:10.1246/bcsj.67.2494

upstream raw materials:

p-toluenesulfonyl chloride

(7E)-(1S,3S,5R,6R)-1-acetoxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclo-9,10-seco-23,24-dinor-7,10⁽¹⁹⁾-cholien-22-ol

(6R)-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclovitamin D₂

(1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclovitamin D₂

Downstream raw materials:

calcitriol

(1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-23-phenylsulfonyl-25-tetrahydropyranyloxy-3,5-cyclovitamin D₃