Methyl 3-azido-2,3,6-trideoxyhexopyranoside

Base Information

• Chemical Name: Methyl 3-azido-2,3,6-trideoxyhexopyranoside
• CAS No.: 56552-71-7
• Molecular Formula: C7H13 N3 O3
• Molecular Weight: 188.2038
• NSC Number: 301728,224965,185342,185339,110346,108082
• DSSTox Substance ID: DTXSID70940505
• Mol file: 56552-71-7.mol

Synonyms:18981-64-1;54623-22-2;DTXSID70940505;NSC108082;NSC110346;NSC185339;NSC185342;NSC224965;NSC301728;NSC-108082;NSC-110346;NSC-185339;NSC-185342;NSC-224965;NSC-301728;methyl 3-azido-2,3,6-trideoxyhexopyranoside;56552-71-7;72002-52-9

Chemical Property of Methyl 3-azido-2,3,6-trideoxyhexopyranoside

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 187.09569129
• Heavy Atom Count: 13
• Complexity: 217

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC)N=[N+]=[N-])O

Technology Process of Methyl 3-azido-2,3,6-trideoxyhexopyranoside

There total 6 articles about Methyl 3-azido-2,3,6-trideoxyhexopyranoside 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:

methanol (67-56-1) + 1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-hexopyranose → methyl 3-azido-2,3,6-trideoxy-α-L-ribo-hexopyranoside (56552-71-7,72002-52-9) + methyl 3-azido-2,3,6-trideoxy-β-L-ribo-hexopyranoside (72002-52-9) + methyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranoside (54623-22-2,72002-52-9) + methyl-3-azido-2,3,6-tridesoxy-β-L-arabino-hexopyranoside (72002-52-9)

Guidance literature:

With K₁₀ montmorillonite; sodium methylate; Yield given. Multistep reaction. Yields of byproduct given; 1.) benzene, reflux, 24 h; 2.) methanol, 6 h;

Reference yield:

methyl α-L-ristosaminide (51869-33-1) → methyl 3-azido-2,3,6-trideoxy-α-L-ribo-hexopyranoside (56552-71-7,72002-52-9)

Guidance literature:

With sodium azide; copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; In methanol; water; toluene; at 20 ℃; for 4h;

DOI:10.1021/jacs.9b01862

Reference yield:

4-O-acetyl-3-azido-2,3,6-trideoxy-L-hexopyranose → methyl 3-azido-2,3,6-trideoxy-α-L-ribo-hexopyranoside (56552-71-7,72002-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / CH₂Cl₂ / 18 h / Ambient temperature

2: 1.) K₁₀ montmorillonite 2.) 1N NaOMe / 1.) benzene, reflux, 24 h; 2.) methanol, 6 h

With pyridine; K₁₀ montmorillonite; sodium methylate; In dichloromethane;

upstream raw materials:

methanol

3,4-di-O-acetyl-6-deoxy-L-glucal

methyl α-L-ristosaminide

Downstream raw materials:

4-Nitro-benzoic acid (2S,3R,4R,6R)-4-azido-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

methyl 3-azido-2,3,6-trideoxy-4-O-methanesulfonyl-α-L-ribo-hexopyranoside