phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside

Base Information

Chemical Name:phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside
CAS No.:819870-57-0
Molecular Formula:C₂₇H₂₇N₃O₅S
Molecular Weight:505.594
Hs Code.:

Synonyms:phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside

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Chemical Property of phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside

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Technology Process of phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside

There total 6 articles about phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside 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: 84.0%

: phenyl 2-azido-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranozide

: 100-39-0
benzyl bromide

: 819870-57-0
phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 5.5h; Inert atmosphere;
DOI:10.1021/jo300722y

Reference yield:

: 183875-22-1
phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside

: 819870-57-0
phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: MeONa / methanol / 20 °C

1.2: 70 percent / camphorsulphonic acid; dimethylanisaldehyde acetal / acetonitrile / 1 h / 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 80 percent / dimethylformamide / 0.67 h / 0 - 20 °C

With sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.06.131

Reference yield:

: 2-azido-2-deoxy-D-glucose

: 819870-57-0
phenyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Cooling with ice

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Inert atmosphere

3: methanol; sodium / 1.5 h / Inert atmosphere

4: camphorsulfonic acid / acetonitrile / 16 h

5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5.5 h / Inert atmosphere

With methanol; trimethylsilyl trifluoromethanesulfonate; camphorsulfonic acid; sodium; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo300722y