(25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3

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Chemical Name:(25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3
CAS No.:1395789-25-9
Molecular Formula:C₃₅H₅₀O₃
Molecular Weight:518.78
Hs Code.:

Synonyms:(25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3

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Chemical Property of (25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3

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Technology Process of (25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3

There total 7 articles about (25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin 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: 91.0%

: 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

: 1395789-25-9
(25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3

Guidance literature:: With methanol; camphor-10-sulfonic acid; at 20 ℃; for 3h; 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

: 1395789-25-9
(25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3

Guidance literature:: Multi-step reaction with 5 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

5.1: camphor-10-sulfonic acid; methanol / 3 h / 20 °C / Inert atmosphere

With methanol; n-butyllithium; dimethylsulfide borane complex; camphor-10-sulfonic acid; 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

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

: 1395789-25-9
(25S)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3

Guidance literature:: Multi-step reaction with 2 steps

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

2: camphor-10-sulfonic acid; methanol / 3 h / 20 °C / Inert atmosphere

With methanol; dimethylsulfide borane complex; camphor-10-sulfonic acid; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran;
DOI:10.1021/jm401989c