2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol

Base Information

• Chemical Name: 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol
• CAS No.: 321541-09-7
• Molecular Formula: C₃₂H₄₉N₃O₅Si₂
• Molecular Weight: 611.929
• Mol file: 321541-09-7.mol

Synonyms:2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol

Chemical Property of 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol

There total 7 articles about 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol 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: 73.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol (321541-08-6) → 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol (321541-09-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at -30 - 20 ℃; for 16h;

DOI:10.1039/b002997l

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol (321541-09-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / imidazole / dimethylformamide / 16 h / -25 - 20 °C

2: 92 percent / pyridine / CH₂Cl₂ / 1.5 h / -15 - 0 °C

3: 71 percent / NaN₃ / dimethylformamide / 1 h / 20 °C

4: 64 percent / NaBH₄ / aq. ethanol / 3 h / 20 °C

5: 73 percent / imidazole / dimethylformamide / 16 h / -30 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b002997l

Reference yield:

Methyl 2,5-anhydro-D-glycero-D-gulo-heptonate (182195-39-7,502685-24-7) → 2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol (321541-09-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / DL-camphor-10-sulfonic acid / acetone / 16 h / 20 °C

2: 72 percent / imidazole / dimethylformamide / 16 h / -25 - 20 °C

3: 92 percent / pyridine / CH₂Cl₂ / 1.5 h / -15 - 0 °C

4: 71 percent / NaN₃ / dimethylformamide / 1 h / 20 °C

5: 64 percent / NaBH₄ / aq. ethanol / 3 h / 20 °C

6: 73 percent / imidazole / dimethylformamide / 16 h / -30 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; camphor-10-sulfonic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1039/b002997l

upstream raw materials:

tert-butylchlorodiphenylsilane

2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-4-deoxy-6,7-O-isopropylidene-D-glycero-D-allo-heptitol

tert-butyldimethylsilyl chloride

Methyl 2,5-anhydro-D-glycero-D-gulo-heptonate

Downstream raw materials:

2,5-Anhydro-4-azido-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-4-deoxy-D-glycero-D-allo-heptitol