3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol

Base Information

• Chemical Name: 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol
• CAS No.: 639808-06-3
• Molecular Formula: C₄₄H₄₇N₃O₄Si
• Molecular Weight: 709.96
• Mol file: 639808-06-3.mol

Synonyms:3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol

Chemical Property of 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol

There total 7 articles about 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol 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:

allyl bromide (106-95-6) + 2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol (639808-05-2) → 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol (639808-06-3)

Guidance literature:

With potassium hexamethyldisilazane; In N,N-dimethyl-formamide; toluene; at 0 - 20 ℃;

DOI:10.1021/jo0349429

Reference yield:

trityl chloride (76-83-5) → 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol (639808-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 16 h

2: 7.8 g / potassium hexamethyldisilazane (KHMDS) / dimethylformamide; toluene / 0 - 20 °C

With pyridine; potassium hexamethyldisilazane; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0349429

Reference yield:

2,5-Anhydro-1,3-O-isopropyliden-6-O-(p-tosyl)-D-glucitol (106248-72-0) → 3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol (639808-06-3)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 16 h / 80 °C

2: 33 g / imidazole / dimethylformamide / 20 °C

3: trifluoroacetic acid / methanol; CH₂Cl₂ / 3 h

4: pyridine / 16 h

5: 7.8 g / potassium hexamethyldisilazane (KHMDS) / dimethylformamide; toluene / 0 - 20 °C

With pyridine; 1H-imidazole; sodium azide; potassium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0349429

upstream raw materials:

allyl bromide

2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-1-O-triphenylmethyl-D-glucitol

trityl chloride

2,5-Anhydro-1,3-O-isopropyliden-6-O-(p-tosyl)-D-glucitol

Downstream raw materials:

E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

3-O-allyl-2,5-anhydro-6-azido-4-O-tert-butyldiphenylsilanyl-6-deoxy-D-glucitol