1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D₃

Base Information

• Chemical Name: 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D₃
• CAS No.: 1439382-04-3
• Molecular Formula: C₃₁H₄₉N₃O₃
• Molecular Weight: 511.748

Synonyms:

Chemical Property of 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D₃

There total 16 articles about 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]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:

C49H91N3O3Si3 (1439381-98-2) → 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D3 (1439382-04-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ml400098w

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-3-C-ethenyl-α-D-altropyranoside → 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D3 (1439382-04-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydroxide; dihydrogen peroxide / 16 h / 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: barium carbonate; N-Bromosuccinimide / tetrachloromethane / 2 h / 0 °C / Reflux

6.1: sodium cyanoborohydride; zinc / propan-1-ol; water / 0.67 h / 20 °C / Reflux

7.1: pyridine / 15.5 h / 0 - 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

9.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

9.2: 2 h / -78 - 20 °C / Inert atmosphere

10.1: potassium carbonate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere

11.1: 2,6-dimethylpyridine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -78 °C / Inert atmosphere

12.2: 1 h / -78 - 20 °C

13.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

14.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 1 h / 110 °C / Inert atmosphere

15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; triethylamine; triphenylphosphine; barium carbonate; sodium hydroxide; zinc; In tetrahydrofuran; methanol; propan-1-ol; tetrachloromethane; hexane; dichloromethane; water; toluene;

DOI:10.1021/ml400098w

Reference yield:

methyl 4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-(2-hydroxyethyl)-α-D-altropyranoside → 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D3 (1439382-04-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2.1: barium carbonate; N-Bromosuccinimide / tetrachloromethane / 2 h / 0 °C / Reflux

3.1: sodium cyanoborohydride; zinc / propan-1-ol; water / 0.67 h / 20 °C / Reflux

4.1: pyridine / 15.5 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

6.2: 2 h / -78 - 20 °C / Inert atmosphere

7.1: potassium carbonate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere

8.1: 2,6-dimethylpyridine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -78 °C / Inert atmosphere

9.2: 1 h / -78 - 20 °C

10.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

11.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 1 h / 110 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; triethylamine; triphenylphosphine; barium carbonate; zinc; In tetrahydrofuran; methanol; propan-1-ol; tetrachloromethane; hexane; dichloromethane; water; toluene;

DOI:10.1021/ml400098w

upstream raw materials:

(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[2-(1H-1,2,3-triazol-1-yl)ethyl]oct-1-en-7-yne

C₄₉H₉₁N₃O₃Si₃

4,6-O-benzylidene-3-deoxy-2-O-(tert-butyldimethylsilyl)-3-C-ethenyl-α-D-altropyranoside

4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

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