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

Base Information

Chemical Name:(25R)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether 25-[(S)-α-methoxy-α-(trifluoromethyl)]phenylacetate
CAS No.:1609168-08-2
Molecular Formula:C₅₇H₈₅F₃O₅Si₂
Molecular Weight:963.465
Hs Code.:

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

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

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

There total 7 articles about (25R)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether 25-[(S)-α-methoxy-α-(trifluoromethyl)]phenylacetate 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: 13.0%

: 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

: 20445-33-4,39637-99-5
(R)-methoxytrifluoromethylphenylacetyl chloride

: 1609168-08-2
(25R)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether 25-[(S)-α-methoxy-α-(trifluoromethyl)]phenylacetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.91667h; Inert atmosphere;
DOI:10.1021/jm401989c

Reference yield:

: 1395789-16-8
1α-hydroxy-2-methylidene-23,23,24,24-tetradehydro-19,25,26,27-tetranorvitamin D3 1,3-bis(tert-butyldimethylsilyl)ether

: 1609168-08-2
(25R)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether 25-[(S)-α-methoxy-α-(trifluoromethyl)]phenylacetate

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 2 h / 0 °C / Inert atmosphere

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

3.1: 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

4.1: triethylamine; dmap / dichloromethane / 2.92 h / 0 - 20 °C / Inert atmosphere

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

Reference yield:

: 610304-70-6
C₄₁H₆₈O₅SSi₂

: 1609168-08-2
(25R)-25-(1-adamantyl)-1α,25-dihydroxy-2-methylidene-23,23,24,24-tetradehydro-19,26,27-trinorvitamin D3 1,3-bis-(tert-butyldimethylsilyl)ether 25-[(S)-α-methoxy-α-(trifluoromethyl)]phenylacetate

Guidance literature:: Multi-step reaction with 6 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

5.1: 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

6.1: triethylamine; dmap / dichloromethane / 2.92 h / 0 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; dimethylsulfide borane complex; methyllithium; potassium carbonate; Dess-Martin periodane; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane;
DOI:10.1021/jm401989c