2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: 2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside
• CAS No.: 1312290-00-8
• Molecular Formula: C₂₉H₃₂N₂O₁₁S
• Molecular Weight: 616.646
• Mol file: 1312290-00-8.mol

Synonyms:2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside

Chemical Property of 2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside

There total 7 articles about 2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-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: 96.0%

2-carboxyphenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside (1312289-98-7) + 3-nitrobenzylamine (7409-18-9) → 2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside (1312290-00-8)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.03.022

Reference yield:

2-(methoxycarbonyl)phenyl 3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside (1312289-96-5) → 2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside (1312290-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: water; sodium hydroxide / methanol / 0.67 h / 20 °C / Inert atmosphere

1.2: acid resin treatment

2.1: pyridine; dmap / 48 h / 20 °C / Inert atmosphere

3.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere

With pyridine; dmap; water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.03.022

Reference yield:

D-galactose pentaacetate (25878-60-8) → 2-(3-nitrobenzylcarbamoyl)phenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside (1312290-00-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 17 h / 20 °C / Inert atmosphere

2.1: methanol; sodium methylate / 20 °C / Inert atmosphere

3.1: di(n-butyl)tin oxide / methanol / 28 h / Inert atmosphere; Reflux

3.2: 3 h / Inert atmosphere; Reflux

4.1: water; sodium hydroxide / methanol / 0.67 h / 20 °C / Inert atmosphere

4.2: acid resin treatment

5.1: pyridine; dmap / 48 h / 20 °C / Inert atmosphere

6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere

With pyridine; methanol; dmap; boron trifluoride diethyl etherate; water; sodium methylate; di(n-butyl)tin oxide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.03.022

upstream raw materials:

2-(methoxycarbonyl)phenyl 3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside

2-carboxyphenyl 3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside

2-carboxyphenyl 2,4,6-tri-O-acetyl-3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside

3-nitrobenzylamine

Downstream raw materials:

2-(3-nitrobenzylcarbamoyl)phenyl 3-O-(prop-2-enyl)-1-thio-β-D-galactopyranoside