methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate

Base Information

• Chemical Name: methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate
• CAS No.: 1345018-86-1
• Molecular Formula: C₂₅H₂₉N₃O₁₂
• Molecular Weight: 563.518
• Mol file: 1345018-86-1.mol

Synonyms:methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate

Chemical Property of methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate

There total 2 articles about methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate 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: 96.0%

methyl 4-azidobenzoate (20442-96-0) + propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (83476-52-2) → methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate (1345018-86-1)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.08.057

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate (1345018-86-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 30 - 50 °C / Inert atmosphere

1.2: 0.75 h

2.1: hydrogenchloride; sodium nitrite / water; acetone / 0 °C

2.2: 5 °C

3.1: copper(ll) sulfate pentahydrate; ascorbic acid / water; N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

With hydrogenchloride; thionyl chloride; copper(ll) sulfate pentahydrate; ascorbic acid; sodium nitrite; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.carres.2012.08.001

Reference yield: 91.0%

methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate (1345018-86-1) → sodium 4-[4-(((α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate (1345019-09-1)

Guidance literature:

methyl 4-[4-(((2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate; With methanol; sodium methylate; at 20 ℃; for 3h; Inert atmosphere;

With sodium hydroxide; In 1,4-dioxane; water; for 16h;

DOI:10.1016/j.bmc.2011.08.057

upstream raw materials:

methyl 4-azidobenzoate

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

4-amino-benzoic acid

Downstream raw materials:

sodium 4-[4-(((α-D-mannopyranosyl)oxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate

methyl-4-[4-((α-D-mannopyranosyloxy)methyl)-1H-1,2,3-triazol-1-yl]benzoate