Methyl 3-azido-2,3,6-trideoxy-4-O-(methanesulfonyl)hexopyranoside

Base Information

• Chemical Name: Methyl 3-azido-2,3,6-trideoxy-4-O-(methanesulfonyl)hexopyranoside
• CAS No.: 87357-49-1
• Molecular Formula: C₈H₁₅N₃O₅S
• Molecular Weight: 265.29
• DSSTox Substance ID: DTXSID50940503
• NSC Number: 185341,109522,108083
• Mol file: 87357-49-1.mol

Synonyms:18981-62-9;DTXSID50940503;Methyl 3-azido-2,3,6-trideoxy-4-O-(methanesulfonyl)hexopyranoside;NSC108083;NSC109522;NSC185341;NSC-108083;NSC-109522;NSC-185341;87357-49-1

Chemical Property of Methyl 3-azido-2,3,6-trideoxy-4-O-(methanesulfonyl)hexopyranoside

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 265.07324176
• Heavy Atom Count: 17
• Complexity: 400

Purity/Quality:

85.0-99.8% ^*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-])OS(=O)(=O)C

Technology Process of Methyl 3-azido-2,3,6-trideoxy-4-O-(methanesulfonyl)hexopyranoside

There total 22 articles about Methyl 3-azido-2,3,6-trideoxy-4-O-(methanesulfonyl)hexopyranoside 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:

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-4-O-methanesulphonyl-α-L-arabino-hexopyranoside (18981-62-9,87357-49-1)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; barium dihydroxide; 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;

DOI:10.1021/jo00174a028

Reference yield:

3,4,5,6-Tetra-O-acetyl-1,2-dideoxy-1-nitro-L-arabino-hexitol (87858-15-9) → methyl 3-azido-2,3,6-trideoxy-4-O-methanesulphonyl-α-L-arabino-hexopyranoside (18981-62-9,87357-49-1)

Guidance literature:

Multi-step reaction with 7 steps

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

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

4: 51 percent / pyridine / refrigerator, overnight

5: 87 percent / AG 1-X₄(OH^-) / methanol / 2 h / Ambient temperature

6: 81 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 2 h / 100 °C

7: 330 mg / pyridine / 6 h / 0 °C

With pyridine; barium dihydroxide; sodium azide; AG 1-X₄(OH^-); AG 50-X₄(H⁺); sulfuric acid; ammonium chloride; In methanol; 2-methoxy-ethanol; water;

DOI:10.1021/jo00174a028

Reference yield:

2-Deoxy-L-arabino-hexose (23568-30-1) → methyl 3-azido-2,3,6-trideoxy-4-O-methanesulphonyl-α-L-arabino-hexopyranoside (18981-62-9,87357-49-1)

Guidance literature:

Multi-step reaction with 6 steps

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

3: 51 percent / pyridine / refrigerator, overnight

4: 87 percent / AG 1-X₄(OH^-) / methanol / 2 h / Ambient temperature

5: 81 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 2 h / 100 °C

6: 330 mg / pyridine / 6 h / 0 °C

With pyridine; sodium azide; AG 1-X₄(OH^-); AG 50-X₄(H⁺); ammonium chloride; In methanol; 2-methoxy-ethanol; water;

DOI:10.1021/jo00174a028

upstream raw materials:

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

methanesulfonyl chloride

methyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranoside

methyl 3-azido-2,3,6-trideoxy-4-O-methoxymethyl-α-L-arabino-hexopyranoside