6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide

Base Information

• Chemical Name: 6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide
• CAS No.: 1057522-11-8
• Molecular Formula: C₂₈H₃₁N₃O₃Si
• Molecular Weight: 485.658
• Mol file: 1057522-11-8.mol

Synonyms:6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide

Chemical Property of 6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide

There total 7 articles about 6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide 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: 64.0%

C26H26O6S (1103726-01-7) + trimethylsilylazide (4648-54-8) → 6-O-trityl-3-deoxy-3-azido-D-galactal (825638-51-5) + 6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide (1057522-11-8)

Guidance literature:

C₂₆H₂₆O₆S; With potassium tert-butylate; In benzene; at 20 ℃; for 0.166667h;

trimethylsilylazide; In benzene; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1016/j.tet.2008.06.039

Reference yield: 30.0%

trimethylsilylazide (4648-54-8) + 4-O-mesyl-6-O-trityl-D-glucal (474459-57-9) → 6-O-trityl-3-deoxy-3-azido-D-galactal (825638-51-5) + 6-O-trityl-3-deoxy-3-azido-D-gulal (825638-48-0) + 6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide (1057522-11-8)

Guidance literature:

4-O-mesyl-6-O-trityl-D-glucal; With potassium tert-butylate; In benzene; at 20 ℃; for 0.166667h;

trimethylsilylazide; With tetramethylguanidinum azide; In benzene; at 20 ℃; for 0.5h;

DOI:10.1021/jo048981b

Reference yield:

1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol (122350-80-5) → 6-O-trityl-4-O-(trimethylsilyloxy)-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl azide (1057522-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide

2.1: pyridine

3.1: TBAF / tetrahydrofuran

4.1: t-BuOK / benzene / 0.17 h / 20 °C

4.2: 30 percent / tetramethylguanidinium azide / benzene / 0.5 h / 20 °C

With pyridine; 1H-imidazole; potassium tert-butylate; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo048981b

upstream raw materials:

trimethylsilylazide

4-O-mesyl-6-O-trityl-D-glucal

1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol

D-glucal

Downstream raw materials:

6-O-trityl-3-deoxy-3-azido-D-galactal