methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)

Base Information

Chemical Name:methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)
CAS No.:1320281-72-8
Molecular Formula:C₂₃H₂₅N₃O₆S
Molecular Weight:471.534
Hs Code.:

Synonyms:methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)

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Chemical Property of methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)

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Technology Process of methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)

There total 6 articles about methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate) 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:

: 1320281-35-3
p-tolyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

: 1320281-72-8
methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)

Guidance literature:: Multi-step reaction with 4 steps

1: methanol; sodium methylate / dichloromethane / 48 h

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h / 0 °C

3: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C

4: pyridine / 1.5 h

With pyridine; methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium methylate; potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol2016862

Reference yield:

: 1320281-41-1
1,4,6-tri-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α/β-D-mannopyranoside

: 1320281-72-8
methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)

Guidance literature:: Multi-step reaction with 5 steps

1: boron trifluoride diethyl etherate / 1,1-dichloroethane / 2 h / 35 °C

2: methanol; sodium methylate / dichloromethane / 48 h

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h / 0 °C

4: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C

5: pyridine / 1.5 h

With pyridine; methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; sodium methylate; potassium carbonate; In 1,1-dichloroethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol2016862

Reference yield:

: 1320281-42-2
p-tolyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

: 1320281-72-8
methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate)

Guidance literature:: Multi-step reaction with 3 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h / 0 °C

2: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C

3: pyridine / 1.5 h

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol2016862