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

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Chemical Name:25R-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether
CAS No.:1395789-20-4
Molecular Formula:C₄₇H₇₈O₃Si₂
Molecular Weight:747.306
Hs Code.:

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

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

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

There total 7 articles about 25R-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-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: 86.0%

: 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

: 1395789-20-4
25R-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

Guidance literature:: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 0 ℃; for 0.833333h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jm401989c

Reference yield:

: 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

: 1395789-18-0
25S-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

: 1395789-20-4
25R-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether

Guidance literature:: With (4R)-2-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine; dimethylsulfide borane complex; In tetrahydrofuran; at 0 ℃; for 1h; Overall yield = 70 %; Overall yield = 4.3 mg; stereoselective reaction; Inert atmosphere;
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

: 1395789-20-4
25R-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-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: 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

4.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 0.83 h / 0 °C / Inert atmosphere

With n-butyllithium; dimethylsulfide borane complex; potassium carbonate; Dess-Martin periodane; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jm401989c