2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• CAS No.: 172471-79-3
• Molecular Formula: C₁₈H₂₉N₃O₄Si
• Molecular Weight: 379.531

Synonyms:2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Chemical Property:

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Technology Process of 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

There total 7 articles about 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 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: 94.0%

2-(trimethylsilyl)ethyl 4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (182273-57-0) → 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (172471-79-3)

Guidance literature:

With methanol; sodium methylate; In dichloromethane;

DOI:10.1039/c9ra08232h

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (172471-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 2,6-di-tert-butyl-4-methylpyridine, silver triflate / CH₂Cl₂ / 0.17 h

2: NaOMe / methanol

With 2,6-di-tert-butyl-4-methylpyridine; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(96)00089-4

Reference yield:

4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl chloride (182273-55-8) → 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (172471-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 2,6-di-tert-butyl-4-methylpyridine, silver triflate / CH₂Cl₂ / 0.17 h

2: NaOMe / methanol

With 2,6-di-tert-butyl-4-methylpyridine; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(96)00089-4

upstream raw materials:

2-(trimethylsilyl)ethyl 4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

2-(Trimethylsilyl)ethanol

4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl chloride

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-5-azido-2-[(2S,3S,4S,5R,6R)-5-azido-4-benzyloxy-6-methyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

C₅₃H₇₂N₂O₁₃Si

2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1→2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

(2R,3S,4S,5R,6R)-5-Amino-2-[(2S,3S,4S,5R,6R)-5-amino-4-benzyloxy-6-methyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-4-benzyloxy-6-methyl-tetrahydro-pyran-3-ol

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