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

Base Information

• Chemical Name: 4,6-O-benzylidene-3-deoxy-2-O-(tert-butyldimethylsilyl)-3-C-ethenyl-α-D-altropyranoside
• CAS No.: 1439381-77-7
• Molecular Formula: C₂₂H₃₄O₅Si
• Molecular Weight: 406.594
• Mol file: 1439381-77-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 4,6-O-benzylidene-3-deoxy-2-O-(tert-butyldimethylsilyl)-3-C-ethenyl-α-D-altropyranoside 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: 85.0%

t-butyldimethylsiyl triflate (69739-34-0) + methyl 4,6-O-benzylidene-3-deoxy-3-C-ethenyl-α-D-altropyranoside → 4,6-O-benzylidene-3-deoxy-2-O-(tert-butyldimethylsilyl)-3-C-ethenyl-α-D-altropyranoside (1439381-77-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ml400098w

Reference yield:

4,6-O-benzylidene-3-deoxy-2-O-(tert-butyldimethylsilyl)-3-C-ethenyl-α-D-altropyranoside (1439381-77-7) → 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-2-yl)ethyl]vitamin D3 (1439382-03-2)

Guidance literature:

Multi-step reaction with 14 steps

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

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

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

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

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

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

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

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

8.2: 2 h / -78 - 20 °C / Inert atmosphere

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

10.1: 2,6-dimethylpyridine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

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

11.2: 1 h / -78 - 20 °C

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

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

14.1: 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:

4,6-O-benzylidene-3-deoxy-2-O-(tert-butyldimethylsilyl)-3-C-ethenyl-α-D-altropyranoside (1439381-77-7) → 1α,25-dihydroxy-2α-[2-(2H-1,2,3-triazol-1-yl)ethyl]vitamin D3 (1439382-04-3)

Guidance literature:

Multi-step reaction with 14 steps

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

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

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

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

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

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

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

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

8.2: 2 h / -78 - 20 °C / Inert atmosphere

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

10.1: 2,6-dimethylpyridine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

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

11.2: 1 h / -78 - 20 °C

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

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

14.1: 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

upstream raw materials:

t-butyldimethylsiyl triflate

Downstream raw materials:

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

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

1α,25-dihydroxy-2α-[2-(1,2,4-triazol-2-yl)ethyl]vitamin D₃

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