5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose

Base Information

• Chemical Name: 5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose
• CAS No.: 340969-92-8
• Molecular Formula: C₃₆H₃₉N₃O₆Si
• Molecular Weight: 637.808

Synonyms:5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose

Chemical Property of 5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose

Chemical Property:

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Technology Process of 5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose

There total 4 articles about 5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose 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: 96.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 5-azido-3-O-benzoyl-4-O-benzyl-5-deoxy-α-L-sorbopyranose (340969-88-2) → 5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose (340969-92-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1016/S0008-6215(00)00319-0

Reference yield:

3-O-benzoyl-4-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose → 5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose (340969-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 84 percent / NaN₃ / dimethylformamide / 15 h / 80 °C

3: 100 mg / TFA / H₂O / 5 h / 20 °C

4: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

With 1H-imidazole; sodium azide; triethylamine; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)00319-0

Reference yield:

5-azido-3-O-benzoyl-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-L-sorbopyranose (340969-82-6) → 5-azido-3-O-benzoyl-4-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose (340969-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 mg / TFA / H₂O / 5 h / 20 °C

2: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

With 1H-imidazole; trifluoroacetic acid; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)00319-0

upstream raw materials:

tert-butylchlorodiphenylsilane

5-azido-3-O-benzoyl-4-O-benzyl-5-deoxy-α-L-sorbopyranose

5-azido-3-O-benzoyl-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-L-sorbopyranose

3-O-benzoyl-4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β-D-fructopyranose

Downstream raw materials:

(3R,4R,5S)-3-benzoyloxy-4-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-1-pyrroline

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