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

Base Information

• Chemical Name: (1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-23-phenylsulfonyl-25-tetrahydropyranyloxy-3,5-cyclovitamin D₃
• CAS No.: 161003-70-9
• Molecular Formula: C₄₅H₆₀O₆S₃
• Molecular Weight: 793.166

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

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

Chemical Property:

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

There total 7 articles about (1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-23-phenylsulfonyl-25-tetrahydropyranyloxy-3,5-cyclovitamin D₃ 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:

(1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclovitamin D2 (161003-63-0) → (1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-23-phenylsulfonyl-25-tetrahydropyranyloxy-3,5-cyclovitamin D3 (161003-70-9)

Guidance literature:

Multi-step reaction with 6 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

5: 100 percent / NaI / acetone / 5 h / Heating

6: 1.) butyllithium, HMPA / 1.) THF, hexane, from -25 to -20 deg C, 20 min, 2.) THF, hexane, -20 deg C, 2 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; ozone; sodium iodide; In ethanol; dichloromethane; acetone;

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)-cholien-22-ol (161003-67-4) → (1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-23-phenylsulfonyl-25-tetrahydropyranyloxy-3,5-cyclovitamin D3 (161003-70-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine / 0 - 5 °C

2: 100 percent / NaI / acetone / 5 h / Heating

3: 1.) butyllithium, HMPA / 1.) THF, hexane, from -25 to -20 deg C, 20 min, 2.) THF, hexane, -20 deg C, 2 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium iodide; In acetone;

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) → (1S,6R)-1-hydroxy-6-(1,3-benzodithiol-2-yloxy)-23-phenylsulfonyl-25-tetrahydropyranyloxy-3,5-cyclovitamin D3 (161003-70-9)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 100 percent / pyridine / 0 - 5 °C

3: 100 percent / NaI / acetone / 5 h / Heating

4: 1.) butyllithium, HMPA / 1.) THF, hexane, from -25 to -20 deg C, 20 min, 2.) THF, hexane, -20 deg C, 2 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; sodium iodide; In ethanol; dichloromethane; acetone;

DOI:10.1246/bcsj.67.2494

upstream raw materials:

2-Methyl-4-phenylsulfonyl-2-<(tetrahydropyran-2-yl)oxy>butan

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

(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

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