beta-D-Glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-, 3-acetate

Base Information

• Chemical Name: beta-D-Glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-, 3-acetate
• CAS No.: 23262-57-9
• Molecular Formula: C₁₆H₂₀N₂O₉
• Molecular Weight: 384.343
• DSSTox Substance ID: DTXSID801154452
• Mol file: 23262-57-9.mol

Synonyms:23262-57-9;beta-D-Glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-, 3-acetate;[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl] acetate;4-Nitrophenyl2-acetamido-3-O-acetyl-2-deoxy-b-D-glucopyranoside;(2S,3R,4R,5S,6R)-3-Acetamido-5-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)tetrahydro-2H-pyran-4-yl acetate;4-Nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-b-D-glucopyranoside;SCHEMBL9185695;DTXSID801154452;(2S,3R,4R,5S,6R)-3-ACETAMIDO-5-HYDROXY-6-(HYDROXYMETHYL)-2-(4-NITROPHENOXY)OXAN-4-YL ACETATE;W-201977;p-Nitrophenyl 2-Acetamido-2-deoxy-3-O-acetyl-?-D-glucopyranoside;P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-ACETYL-BETA-D-GLUCOPYRANOSIDE;[(2R, 3S, 4R, 5R, 6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl] acetate

Chemical Property of beta-D-Glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-, 3-acetate

Chemical Property:

• Melting Point: 185-187?C
• PSA: 160.14000
• LogP: 0.40220
• Solubility.: DMF, DMSO
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 384.11688022
• Heavy Atom Count: 27
• Complexity: 545

Purity/Quality:

99%, ^*data from raw suppliers

4-Nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)OC(=O)C
• Uses: p-Nitrophenyl 2-Acetamido-2-deoxy-3-O-acetyl-β-D-glucopyranoside (cas# 23262-57-9) is a compound useful in organic synthesis.

Technology Process of beta-D-Glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-, 3-acetate

There total 1 articles about beta-D-Glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-, 3-acetate 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:

→ 4-nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside (23262-57-9)

Guidance literature:

4,6-Benzyliden-Verbindung 6, Essigsaeure;

DOI:10.1016/S0008-6215(00)82136-9

Reference yield: 85.7%

4-nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside (23262-57-9) + Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside (130572-02-0) → Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester (130572-14-4)

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide;

DOI:10.1016/S0040-4039(00)97612-3

Reference yield:

4-nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside (23262-57-9) → p-nitrophenyl 2-acetamido-2-deoxy-6-O-α-L-fucopyranosyl-β-D-glucopyranoside (81340-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85.7 percent / CuBr₂, Bu₄NBr

2: 79.8 percent / CHCl₃, TFA, H₂O, MeOH, MeONa

With methanol; chloroform; tetrabutylammomium bromide; water; sodium methylate; trifluoroacetic acid; copper(ll) bromide;

DOI:10.1016/S0040-4039(00)97612-3

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

p-nitrophenyl 2-acetamido-2-deoxy-6-O-α-L-fucopyranosyl-β-D-glucopyranoside

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