(2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate
• CAS No.: 1448330-50-4
• Molecular Formula: C₂₇H₃₄N₂O₁₃
• Molecular Weight: 594.573

Synonyms:

Chemical Property of (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate

There total 6 articles about (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate 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: 47.0%

(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate (1448330-49-1) + tiolacetic acid (507-09-5) → (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate (1448330-50-4)

Guidance literature:

at 20 ℃; for 12h;

DOI:10.1039/c3cc42836b

Reference yield:

D-(+)-galactosamine hydrochloride (1772-03-8,4710-95-6,6730-09-2,14131-59-0,14131-62-5,14131-63-6,14131-65-8,14131-67-0,14257-79-5,19124-46-0,20706-90-5,91673-92-6) → (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate (1448330-50-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(ll) sulfate pentahydrate / methanol / 18 h / 20 °C

2.1: pyridine / 3 h / 20 °C

3.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 0.5 h / 20 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

5.1: dichloromethane / 0.5 h / -20 °C / Molecular sieve

5.2: 2 h / -20 °C / Molecular sieve

6.1: 12 h / 20 °C

With pyridine; imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; hydrazinium monoacetate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c3cc42836b

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (84278-00-2) → (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate (1448330-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 0.5 h / 20 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C

3.1: dichloromethane / 0.5 h / -20 °C / Molecular sieve

3.2: 2 h / -20 °C / Molecular sieve

4.1: 12 h / 20 °C

With hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c3cc42836b

upstream raw materials:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate

(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenoxy)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

tiolacetic acid

D-(+)-galactosamine hydrochloride

Downstream raw materials:

(2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(1-(4-((E)-(4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10,13-tetraoxo-8,14-dioxa-2,6,11-triazaheptadec-16-en-9-yl)phenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate

9-(4-(((2R,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-1-(4-((E)-(4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oic acid

(2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate

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