1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole

Base Information

• Chemical Name: 1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole
• CAS No.: 1033538-05-4
• Molecular Formula: C₁₈H₂₃N₃O₅
• Molecular Weight: 361.398
• Mol file: 1033538-05-4.mol

Synonyms:1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole

Chemical Property of 1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole

There total 4 articles about 1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole 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: 94.0%

5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (131053-15-1) + propargyl alcohol (107-19-7) → 1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole (1033538-05-4)

Guidance literature:

With copper(II) sulfate; sodium L-ascorbate; In water; tert-butyl alcohol; at 30 ℃; for 3.5h;

DOI:10.1016/j.carres.2008.02.013

Reference yield: 46.0%

5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (131053-15-1) + propargyl alcohol (107-19-7) → 1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole (1033538-05-4) + 3-O-benzyl-5-deoxy-5-(5-hydroxymethyl-1H-1,2,3-triazol-1-yl)-1,2-O-isopropylidene-α-D-xylofuranose

Guidance literature:

In toluene; at 110 ℃; for 24h; Inert atmosphere;

DOI:10.1002/cplu.202000424

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) → 1-(3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranos-5-yl)-4-hydroxymethyl-1H-1,2,3-triazole (1033538-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 16 h / 20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

3: toluene / 24 h / 110 °C / Inert atmosphere

With pyridine; sodium azide; In N,N-dimethyl-formamide; toluene;

DOI:10.1002/cplu.202000424

upstream raw materials:

5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose

propargyl alcohol

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

O-benzyl-1,2-di-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-xylofuranose