4-Nitrophenyl 2-Acetamido-3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl) -2-deoxy-α-D-galactopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl 2-Acetamido-3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl) -2-deoxy-α-D-galactopyranoside
• CAS No.: 1144040-11-8
• Molecular Formula: C30H44N4O18
• Molecular Weight: 748.695
• Mol file: 1144040-11-8.mol

Synonyms:4-Nitrophenyl 2-Acetamido-3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl) -2-deoxy-α-D-galactopyranoside;4-Nitrophenyl O-2-(AcetylaMino)-2-deoxy-β-D-glucopyranosyl-(1-3)-O -[2-(acetylaMino)-2-deoxy-β-D-glucopyranosyl-(1-6)]-2-(acetylaMino)-2-deoxy-α-D-galactopyranoside;GlcNAcβ(1-3){GlcNAcβ(1-6)}GalNAcα(1-O)PNP

Chemical Property of 4-Nitrophenyl 2-Acetamido-3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl) -2-deoxy-α-D-galactopyranoside

Chemical Property:

• Boiling Point: 1186.5±65.0 °C(Predicted)
• PKA: 12.63±0.70(Predicted)
• PSA: 340.58000
• Density: 1.58±0.1 g/cm3(Predicted)
• LogP: -2.10260

Purity/Quality:

97% ^*data from raw suppliers

N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4R,5R,6R)-5-Acetamido-4-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-6-(4-nitrophenoxy)oxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An analogue of p-nitrophenyl T-antigen as potential substrate for elucidation of the substrate specificity of endo-α- N-acetylgalactosaminidase. An analogue of p-nitrophenyl T-antigen as potential substrate for elucidation of the substrate specificity of endo-α-N-acetylgalactosaminidase.

Technology Process of 4-Nitrophenyl 2-Acetamido-3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl) -2-deoxy-α-D-galactopyranoside

There total 11 articles about 4-Nitrophenyl 2-Acetamido-3,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl) -2-deoxy-α-D-galactopyranoside 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:

p-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside (1147438-51-4) → p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-galactopyranoside (1144040-11-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium methylate / methanol / 0.5 h / 20 °C / pH 10

1.2: Dowex H+

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; acetonitrile / 1 h / 20 °C

3.1: N-iodo-succinimide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 1 h / -30 °C / Inert atmosphere; Molecular sieve

4.1: water; acetic acid / dichloromethane / 48 h / 20 °C

5.1: N-iodo-succinimide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

5.2: 1 h / -30 °C / Inert atmosphere; Molecular sieve

6.1: sodium methylate / methanol / 0.33 h / 20 °C

6.2: Dowex H+

7.1: hydrazine / ethanol / 70 °C

8.1: dmap / pyridine / 2 h / 20 °C

9.1: pyridine / 20 °C

10.1: sodium methylate / methanol / 0.5 h

10.2: 1 h

10.3: Dowex H+

With dmap; N-iodo-succinimide; water; sodium methylate; toluene-4-sulfonic acid; acetic acid; hydrazine; In pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2011.03.036

Reference yield:

p-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-4,6-O-p-methoxybenzylidene-α-D-galactopyranoside (1316823-20-7) → p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-galactopyranoside (1144040-11-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: water; acetic acid / dichloromethane / 48 h / 20 °C

2.1: N-iodo-succinimide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 1 h / -30 °C / Inert atmosphere; Molecular sieve

3.1: sodium methylate / methanol / 0.33 h / 20 °C

3.2: Dowex H+

4.1: hydrazine / ethanol / 70 °C

5.1: dmap / pyridine / 2 h / 20 °C

6.1: pyridine / 20 °C

7.1: sodium methylate / methanol / 0.5 h

7.2: 1 h

7.3: Dowex H+

With dmap; N-iodo-succinimide; water; sodium methylate; acetic acid; hydrazine; In pyridine; methanol; ethanol; dichloromethane;

DOI:10.1016/j.carres.2011.03.036

Reference yield:

p-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranoside (1316823-24-1) → p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-galactopyranoside (1144040-11-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-iodo-succinimide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

1.2: 1 h / -30 °C / Inert atmosphere; Molecular sieve

2.1: sodium methylate / methanol / 0.33 h / 20 °C

2.2: Dowex H+

3.1: hydrazine / ethanol / 70 °C

4.1: dmap / pyridine / 2 h / 20 °C

5.1: pyridine / 20 °C

6.1: sodium methylate / methanol / 0.5 h

6.2: 1 h

6.3: Dowex H+

With dmap; N-iodo-succinimide; sodium methylate; hydrazine; In pyridine; methanol; ethanol; dichloromethane;

DOI:10.1016/j.carres.2011.03.036

upstream raw materials:

p-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside

p-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-4,6-O-p-methoxybenzylidene-α-D-galactopyranoside

p-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranoside

p-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-2-azido-2-deoxy-α-D-galactopyranoside

Downstream raw materials:

p-aminophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-galactopyranoside

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