p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside

Base Information

• Chemical Name: p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside
• CAS No.: 251365-48-7
• Molecular Formula: C₃₃H₄₃NO₁₉
• Molecular Weight: 757.7
• Mol file: 251365-48-7.mol

Synonyms:p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside

Chemical Property of p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside

There total 2 articles about p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside 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: 82.0%

pivaloyl chloride (3282-30-2) + p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-β-lactoside (148705-02-6) → p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside (251365-48-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1016/S0968-0896(99)00129-7

Reference yield:

4-nitrophenyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (148705-01-5) → p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside (251365-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ethylene glycol; TMSCl / CH₂Cl₂; methanol / 5 h

2: 82 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With dmap; chloro-trimethyl-silane; ethylene glycol; triethylamine; In methanol; dichloromethane; 1: Ring cleavage / 2: Acylation;

DOI:10.1016/S0968-0896(99)00129-7

Reference yield: 79.0%

p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-3'-O-pivaloyl-β-lactoside (251365-48-7) + 2-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (382141-77-7) → 2,2-dimethyl-propionic acid 3-acetoxy-6-acetoxymethyl-2-[4,5-diacetoxy-2-acetoxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-5-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; at -10 ℃; for 3h;

DOI:10.1055/s-2001-16803

upstream raw materials:

pivaloyl chloride

p-nitrophenyl 2,3,6,2',6'-penta-O-acetyl-β-lactoside

4-nitrophenyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

p-nitrophenyl O-[6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->4)-2,6-di-O-acetyl-3-O-pivaloyl-β-D-galactopyranosyl)]-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

p-aminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside

p-acryloylaminophenyl O-[α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranoside