3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose

Base Information

• Chemical Name: 3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose
• CAS No.: 551934-09-9
• Molecular Formula: C₁₈H₂₃N₃O₈S
• Molecular Weight: 441.462
• Mol file: 551934-09-9.mol

Synonyms:3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose

Chemical Property of 3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose

There total 2 articles about 3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + 3-azido-5-O-acetyl-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-ribofuranose (551934-06-6) → 3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose (551934-09-9)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/S0040-4020(02)01632-0

Reference yield:

3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1) → 3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose (551934-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Candida antarctica lipase / toluene / 25 - 28 °C

2: 95 percent / pyridine / 0 °C

With pyridine; Candida antarctica lipase; In toluene;

DOI:10.1016/S0040-4020(02)01632-0

Reference yield:

acetic anhydride (108-24-7) + 3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose (551934-09-9) → 5-O-acetoxy-1,2-di-O-acetyl-3-azido-3-deoxy-4-C-(p-toluenesulphonyloxymethyl)-β-D-ribofuranose + 5-O-acetoxy-1,2-di-O-acetyl-3-azido-3-deoxy-4-C-(p-toluenesulphonyloxymethyl)-α-D-ribofuranose

Guidance literature:

With sulfuric acid; acetic acid; for 5h; Overall yield = 94 %; Overall yield = 6.2 g;

DOI:10.1039/c4ra06805j

upstream raw materials:

p-toluenesulfonyl chloride

3-azido-5-O-acetyl-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-ribofuranose

3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose