1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3

Base Information

• Chemical Name: 1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3
• CAS No.: 1307302-42-6
• Molecular Formula: C₄₃H₇₄O₅Si
• Molecular Weight: 699.143
• Mol file: 1307302-42-6.mol

Synonyms:1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3

Chemical Property of 1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3

There total 6 articles about 1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin 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: 74.0%

3,4-dihydro-2H-pyran (110-87-2) + 1α-[((trimethylsilyl)-oxy)]-3β-[((tertiary-butyl-dimethylsilyl)-oxy)], 25-trihydroxy-9,10-5(Z),7(E),10(19)-triene (132054-64-9) → 1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3 (1307302-42-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1016/j.bmcl.2011.02.025

Reference yield:

calcidiol (19356-17-3) → 1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3 (1307302-42-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sulfur dioxide / Reflux

2.1: 1H-imidazole / N,N-dimethyl-formamide

3.1: sodium hydrogencarbonate / ethanol / Reflux

4.1: selenium(IV) oxide / dichloromethane / 0.5 h / Reflux; Inert atmosphere

4.2: 1 h / Reflux; Inert atmosphere

5.1: anthracene; triethylamine / toluene / 1.25 h / UV-irradiation

6.1: pyridinium p-toluenesulfonate / dichloromethane

With 1H-imidazole; selenium(IV) oxide; anthracene; sulfur dioxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2011.02.025

Reference yield:

1α,25-dihydroxy-5E-vitamin D3-3β-tert-butyldimethylsilyl ether (132054-64-9) → 1α,25-di-tetrahydropyranyloxy-3β-tert-butyldimethysilyl-5Z-vitamin D3 (1307302-42-6)

Guidance literature:

Multi-step reaction with 2 steps

1: anthracene; triethylamine / toluene / 1.25 h / UV-irradiation

2: pyridinium p-toluenesulfonate / dichloromethane

With anthracene; pyridinium p-toluenesulfonate; triethylamine; In dichloromethane; toluene;

DOI:10.1016/j.bmcl.2011.02.025

upstream raw materials:

3,4-dihydro-2H-pyran

1α-[((trimethylsilyl)-oxy)]-3β-[((tertiary-butyl-dimethylsilyl)-oxy)], 25-trihydroxy-9,10-5(Z),7(E),10(19)-triene

calcidiol

25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether

Downstream raw materials:

1α,25-di-tetrahydropyranyloxy-5Z-vitamin D3

C₃₉H₆₁BrO₆