Methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxyhexopyranoside

Base Information

• Chemical Name: Methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxyhexopyranoside
• CAS No.: 20744-42-7
• Molecular Formula: C₁₈H₂₁N₃O₈
• Molecular Weight: 407.38
• NSC Number: 116268
• DSSTox Substance ID: DTXSID90942960
• Mol file: 20744-42-7.mol

Synonyms:20744-42-7;DTXSID90942960;Methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxyhexopyranoside;NSC116268;NSC-116268

Chemical Property of Methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxyhexopyranoside

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 407.13286464
• Heavy Atom Count: 29
• Complexity: 645

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OC)CN=[N+]=[N-])OC(=O)C2=CC=CC=C2

Technology Process of Methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxyhexopyranoside

There total 1 articles about Methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxyhexopyranoside 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:

→ methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxy-α-D-mannopyranoside (20744-42-7)

Guidance literature:

aus Methyl-2,O³-diacetyl-O⁴-benzoyl-6-brom-6-desoxy-α-D-mannopyranosid>und NaN3;

DOI:10.1016/S0008-6215(00)81444-5

Reference yield: 80.0%

methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxy-α-D-mannopyranoside (20744-42-7) + acetic anhydride (108-24-7) → 1,2,3-tri-O-acetyl-6-azido-4-O-benzoyl-6-deoxy-α-D-mannopyranose

Guidance literature:

With sulfuric acid; for 60h; Ambient temperature;

Reference yield:

methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxy-α-D-mannopyranoside (20744-42-7) → 6-azido-6-deoxy-D-talose (138332-00-0,138332-01-1)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₃ONa, methanol

2: 97 percent / p-toluenesulfonic acid / 1.5 h / Ambient temperature

3: 82 percent / RuO₂, NaIO₄ / H₂O; CCl₄ / 8 h

4: 75 percent / NaBH₄ / methanol; H₂O / 1 h / 5 °C

5: 88.5 percent / aq.HCl / 3.5 h / 90 - 110 °C

With hydrogenchloride; methanol; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; sodium methylate; toluene-4-sulfonic acid; In methanol; tetrachloromethane; water;

Downstream raw materials:

methyl 6-azido-6-deoxy-α-D-mannopyranoside

6-azido-6-deoxy-D-talose