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

Base Information

• Chemical Name: methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside
• CAS No.: 1155874-64-8
• Molecular Formula: C₁₄H₂₀N₂O₄
• Molecular Weight: 280.324
• Mol file: 1155874-64-8.mol

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

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

There total 7 articles about methyl 2,3-diamino-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: 59.0%

methyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside (287719-31-7) → methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside (1155874-64-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/om5013117

Reference yield:

Toluene-4-sulfonic acid (2R,4aR,6S,7S,8S,8aR)-7-azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside (1155874-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide / N,N-dimethyl-formamide; 1,4-dioxane / 40 h / Reflux

2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C

With lithium aluminium tetrahydride; sodium azide; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/om5013117

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranoside (1155874-64-8)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 14 h / 0 - 4 °C

2: sodium methylate / methanol / 14 h / Reflux

3: sodium azide; ammonium chloride / 2-methoxy-ethanol; water / 8.5 h / Reflux

4: pyridine; dmap / dichloromethane / 168 h / 0 - 20 °C / Reflux

5: sodium azide / N,N-dimethyl-formamide; 1,4-dioxane / 40 h / Reflux

6: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C

With pyridine; dmap; lithium aluminium tetrahydride; sodium azide; sodium methylate; ammonium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/om5013117

upstream raw materials:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

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

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

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