25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

Base Information

Chemical Name:25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether
CAS No.:1395789-64-6
Molecular Formula:C₄₇H₇₆O₃Si₂
Molecular Weight:745.29
Hs Code.:

Synonyms:25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

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Chemical Property of 25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

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Technology Process of 25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

There total 5 articles about 25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether 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: 84.0%

: 25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

: 1395789-64-6
25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jm401989c

Reference yield:

: 610304-70-6
C₄₁H₆₈O₅SSi₂

: 1395789-64-6
25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

Guidance literature:: Multi-step reaction with 4 steps

1.1: methyllithium / 1,4-dioxane; hexane / 0.5 h / 0 °C / Inert atmosphere

1.2: 15 h / 105 °C / Inert atmosphere; Sealed tube

2.1: potassium carbonate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / hexane / 0.12 h / 0 °C / Inert atmosphere

3.2: 2 h / 0 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C / Inert atmosphere

With n-butyllithium; methyllithium; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane;
DOI:10.1021/jm401989c

Reference yield:

: 1395789-14-6
1α-hydroxy-2-methylidene-24-trimethylsilyl-23,23,24,24-tetradehydro-19,25,26,27-tetranorvitamin D3 1,3-is(tert-butyldimethylsilyl)ether

: 1395789-64-6
25-(1-adamantyl)-1α-hydroxy-2-methylidene-25-oxo-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium carbonate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / hexane / 0.12 h / 0 °C / Inert atmosphere

2.2: 2 h / 0 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C / Inert atmosphere

With n-butyllithium; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jm401989c