(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

Base Information

• Chemical Name: (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
• CAS No.: 1448330-49-1
• Molecular Formula: C₂₅H₃₀N₄O₁₂
• Molecular Weight: 578.533

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Safty Information:

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Technology Process of (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

There total 5 articles about (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 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: 53.0%

allyl 2-(2-hydroxy-2-(4-hydroxyphenyl)acetamido)acetate (1316832-58-2) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate (83025-11-0) → (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)

Guidance literature:

allyl 2-(2-hydroxy-2-(4-hydroxyphenyl)acetamido)acetate; 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate; In dichloromethane; at -20 ℃; for 0.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 2h; Molecular sieve;

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)-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)

Guidance literature:

Multi-step reaction with 5 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

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)-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)

Guidance literature:

Multi-step reaction with 3 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

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:

allyl 2-(2-hydroxy-2-(4-hydroxyphenyl)acetamido)acetate

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

D-(+)-galactosamine hydrochloride

2-azido-2-deoxy-D-galactose

Downstream raw materials:

(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

(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-hydroxy-2-oxoethyl)phenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate

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