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

Base Information

• Chemical Name: 4-(4-nitrophenyloxythionocarbonyloxy)-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS No.: 1283072-92-3
• Molecular Formula: C₂₅H₂₉NO₁₄S
• Molecular Weight: 599.57
• Mol file: 1283072-92-3.mol

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

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

There total 1 articles about 4-(4-nitrophenyloxythionocarbonyloxy)-2Z-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: 70.0%

4-nitrophenyl chlorothionoformate (1132-69-0) + 2-butene-1-ol-4-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (500219-26-1) → 4-(4-nitrophenyloxythionocarbonyloxy)-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-92-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃;

DOI:10.1021/jo102411j

Reference yield: 73.0%

4-(4-nitrophenyloxythionocarbonyloxy)-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-92-3) + N-(2-azidoethyl)-N-benzylamine (150651-47-1) → 4-[N-(2-azidoethyl)-N-(benzyl)thionocarbamoyloxy]-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-93-4)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃;

DOI:10.1021/jo102411j

Reference yield:

4-(4-nitrophenyloxythionocarbonyloxy)-2Z-butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1283072-92-3) → C22H32O10S3

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap / dichloromethane / 20 °C

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

3.1: sodium methylate / methanol / 0.5 h / 20 °C

4.1: triphenylphosphine / tetrahydrofuran / 0.5 h / Reflux

4.2: 0.5 h / 20 °C

5.1: methanol / 20 °C / Inert atmosphere

With dmap; palladium chloride*2MeCN; sodium methylate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo102411j

upstream raw materials:

4-nitrophenyl chlorothionoformate

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

Downstream raw materials:

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

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

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