2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS No.: 1283072-95-6
• Molecular Formula: C₂₈H₃₆N₄O₁₁S
• Molecular Weight: 636.68
• Mol file: 1283072-95-6.mol

Synonyms:2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Chemical Property of 2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

There total 3 articles about 2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 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: 99.0%

4-[N-(2-azidoethyl)-N-(benzyl)thionocarbamoyloxy]-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-93-4) → 2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-95-6)

Guidance literature:

With palladium chloride*2MeCN; In dichloromethane; at 40 ℃; for 20h;

DOI:10.1021/jo102411j

Reference yield:

4-(4-nitrophenyloxythionocarbonyloxy)-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-92-3) → 2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / dichloromethane / 20 °C

2: palladium chloride*2MeCN / dichloromethane / 20 h / 40 °C

With dmap; palladium chloride*2MeCN; In dichloromethane;

DOI:10.1021/jo102411j

Reference yield:

2-butene-1-ol-4-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (500219-26-1) → 2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-95-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; dmap / dichloromethane / 20 °C

2: dmap / dichloromethane / 20 °C

3: palladium chloride*2MeCN / dichloromethane / 20 h / 40 °C

With pyridine; dmap; palladium chloride*2MeCN; In dichloromethane;

DOI:10.1021/jo102411j

upstream raw materials:

4-(4-nitrophenyloxythionocarbonyloxy)-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2-butene-1-ol-4-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

4-[N-(2-azidoethyl)-N-(benzyl)thionocarbamoyloxy]-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

2-[N-(2-azidoethyl)-N-(benzyl)carbamoylthio]-3-butenyl β-D-glucopyranoside