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

Base Information

• Chemical Name: Methyl 3-azido-2,3,6-trideoxyhexopyranoside
• CAS No.: 72002-52-9
• Molecular Formula: C₇H₁₃N₃O₃
• Molecular Weight: 187.199
• NSC Number: 301728,224965,185342,185339,110346,108082
• DSSTox Substance ID: DTXSID70940505
• Mol file: 72002-52-9.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:

99% ^*data from raw suppliers

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 93 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: 98.0%

methyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-lyxo-hexopyranoside (127301-32-0) → Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (18981-64-1,72002-52-9)

Guidance literature:

With sodium methylate; In methanol; for 48h;

Reference yield: 46.0%

Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 4-benzoate (19129-68-1) → Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (18981-64-1,72002-52-9)

Guidance literature:

With sodium hydroxide; In methanol; water; for 6.5h; Ambient temperature;

DOI:10.1021/jo00174a028

Reference yield:

3,4,5,6-Tetra-O-acetyl-1,2-dideoxy-1-nitro-L-arabino-hex-1-enitol (87858-14-8) → Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (18981-64-1,72002-52-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / H₂ / 10percent Pd/C / ethyl acetate / Ambient temperature

2: 1) Ba(OH)2*8H₂O, 2) H₂SO₄ / 1) water, room temp., 2) <10 degC -> room temp., overnight

3: AG 50-X₄(H⁺) / 120 h / Ambient temperature

5: 51 percent / pyridine / refrigerator, overnight

6: 87 percent / AG 1-X₄(OH^-) / methanol / 2 h / Ambient temperature

7: 81 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 2 h / 100 °C

8: 330 mg / pyridine / 6 h / 0 °C

9: 170 mg / dimethylformamide / 28 h / 135 °C

10: 46 percent / 0.1 N NaOH / methanol; H₂O / 6.5 h / Ambient temperature

With pyridine; barium dihydroxide; sodium hydroxide; sodium azide; AG 1-X₄(OH^-); AG 50-X₄(H⁺); sulfuric acid; hydrogen; ammonium chloride; palladium on activated charcoal; In methanol; 2-methoxy-ethanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00174a028

upstream raw materials:

methyl-3,4-anhydro-2,6-didesoxy-β-L-lyxo-hexopyranoside

methyl-2,6-didesoxy-β-L-arabino-hexopyranoside

methyl-3,4-di-O-acetyl-2,6-didesoxy-β-L-arabino-hexopyranoside

methyl-3-O-benzoyl-2,6-didesoxy-β-L-arabino-hexopyranoside

Downstream raw materials:

(2R,3R,4R,6S)-4-Azido-6-methoxy-2-methyl-tetrahydro-pyran-3-ol

3-Azido-1,4-di-O-(p-nitrobenzoyl)-2,3,6-trideoxy-α,β-L-arabino-hexopyranose