methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside
• CAS No.: 287719-31-7
• Molecular Formula: C₁₄H₁₆N₆O₄
• Molecular Weight: 332.319
• Mol file: 287719-31-7.mol

Synonyms:methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside

Chemical Property of methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside

There total 6 articles about methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-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:

methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(trifluoromethanesulfonyl)-α-D-altropyranoside (207506-27-2) → methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside (287719-31-7)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; Yield given;

DOI:10.1021/jo00117a016

Reference yield:

2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside (116003-77-1) → methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside (287719-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 1,2-dichloro-ethane / 0.5 h

2: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 80 °C

With pyridine; sodium azide; ammonium chloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo201179p

Reference yield:

methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside (65530-21-4) → methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside (287719-31-7)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide / tetrahydrofuran; methanol / 70 °C

2: sodium azide; ammonium chloride / dimethyl sulfoxide / 80 °C

3: pyridine / 1,2-dichloro-ethane / 0.5 h

4: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 80 °C

With pyridine; sodium azide; ammonium chloride; potassium hydroxide; In tetrahydrofuran; methanol; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo201179p

upstream raw materials:

methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(trifluoromethanesulfonyl)-α-D-altropyranoside

2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside

methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

Downstream raw materials:

methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside

Acetic acid (2R,3S,4R,5S,6S)-4,5-diazido-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

methyl 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-α-D-mannopyranoside