phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside
• CAS No.: 402831-58-7
• Molecular Formula: C₁₉H₁₉N₃O₄S
• Molecular Weight: 385.444
• Mol file: 402831-58-7.mol

Synonyms:phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside

There total 6 articles about phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside 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: 91.0%

benzaldehyde dimethyl acetal (1125-88-8) + phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside (166516-71-8) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside (402831-58-7)

Guidance literature:

With tetrafluoroboric acid dimethyl ether complex; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)01880-9

Reference yield:

D-mannosamine hydrochloride (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) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside (402831-58-7)

Guidance literature:

Multi-step reaction with 5 steps

1: TfN₃; K₂CO₃ / CuSO₄ / H₂O; methanol; CH₂Cl₂

2: pyridine / DMAP

3: 70 percent / BF₃*OEt₂ / CH₂Cl₂ / 35 °C

4: 100 percent / KOtBu / methanol

5: 91 percent / HBF₄*OMe₂ / dimethylformamide

With pyridine; triflic azide; boron trifluoride diethyl etherate; potassium tert-butylate; potassium carbonate; tetrafluoroboric acid dimethyl ether complex; dmap; copper(II) sulfate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)01880-9

Reference yield:

2-azido-2-deoxy-D-mannopyranose (97604-58-5) → phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside (402831-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / DMAP

2: 70 percent / BF₃*OEt₂ / CH₂Cl₂ / 35 °C

3: 100 percent / KOtBu / methanol

4: 91 percent / HBF₄*OMe₂ / dimethylformamide

With pyridine; boron trifluoride diethyl etherate; potassium tert-butylate; tetrafluoroboric acid dimethyl ether complex; dmap; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)01880-9

upstream raw materials:

benzaldehyde dimethyl acetal

phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside

D-mannosamine hydrochloride

2-azido-2-deoxy-D-mannopyranose

Downstream raw materials:

phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside