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

Base Information

• Chemical Name: 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
• CAS No.: 172471-69-1
• Molecular Formula: C₃₃H₄₆N₆O₈Si
• Molecular Weight: 682.849

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 82.0%

2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl chloride (115479-43-1) + 2-(trimethylsilyl)ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside (172471-79-3) → 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 (172471-69-1)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; for 1h; Ambient temperature;

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

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → 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 (172471-69-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: NaOMe / methanol

3: 82 percent / silver triflate, 2,4,6-trimethylpyridine / CH₂Cl₂ / 1 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; 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) → 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 (172471-69-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: NaOMe / methanol

3: 82 percent / silver triflate, 2,4,6-trimethylpyridine / CH₂Cl₂ / 1 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; 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-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl chloride

2-(trimethylsilyl)ethyl 4-azido-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

Downstream raw materials:

(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

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-mannopyranosyl)-(1-> 2)]₂-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside

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

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