ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside
• CAS No.: 297733-55-2
• Molecular Formula: C₁₅H₁₈N₆O₃S
• Molecular Weight: 362.412
• Mol file: 297733-55-2.mol

Synonyms:ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside

Chemical Property of ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside

There total 5 articles about ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside 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:

Trifluoro-methanesulfonic acid (2R,4aR,6S,7S,8S,8aR)-7-azido-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside (297733-55-2)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 20 ℃; for 0.5h;

DOI:10.1016/S0008-6215(99)00318-3

Reference yield:

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8) → ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside (297733-55-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / pyridine / 70 h / 20 °C

2: Bu₄NHSO₄; NaOH; K₂CO₃ / toluene; dimethylsulfoxide; butan-1-ol / 2 h / 20 °C

3: NaN₃; NH₄Cl / dimethylsulfoxide / 20 h / 80 °C

4: CH₂Cl₂; pyridine / 2.5 h / 0 - 20 °C

5: NaN₃ / dimethylsulfoxide / 0.5 h / 20 °C

With sodium hydroxide; sodium azide; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; ammonium chloride; In pyridine; dichloromethane; dimethyl sulfoxide; toluene; butan-1-ol; 1: Tosylation / 2: Substitution / 3: Substitution / 4: Acylation / 5: Substitution;

DOI:10.1016/S0008-6215(99)00318-3

Reference yield:

(1aR,2S,3aR,6R,7aR,7bR)-2-Ethylsulfanyl-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene (297733-53-0) → ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside (297733-55-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃; NH₄Cl / dimethylsulfoxide / 20 h / 80 °C

2: CH₂Cl₂; pyridine / 2.5 h / 0 - 20 °C

3: NaN₃ / dimethylsulfoxide / 0.5 h / 20 °C

With sodium azide; ammonium chloride; In pyridine; dichloromethane; dimethyl sulfoxide; 1: Substitution / 2: Acylation / 3: Substitution;

DOI:10.1016/S0008-6215(99)00318-3

upstream raw materials:

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

(1aR,2S,3aR,6R,7aR,7bR)-2-Ethylsulfanyl-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-altropyranoside

ethyl 4,6-O-benzylidene-3-O-p-toluenesulfonyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

N-{4-[2-((2R,4aR,6S,7S,8R,8aS)-7,8-Diazido-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-ethyl]-phenyl}-2,2,2-trifluoro-acetamide

2-(p-trifluoroacetamidophenyl)ethyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-2,3-diacetamido-6-O-benzyl-2,3-dideoxy-α-D-mannopyranoside

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5S,6S)-4,5-bis-acetylamino-2-formyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

2-(p-trifluoroacetamidophenyl)ethyl 2,3-diazido-6-O-benzyl-2,3-dideoxy-α-D-mannopyranoside