p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside

Base Information

• Chemical Name: p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside
• CAS No.: 765308-76-7
• Molecular Formula: C₃₄H₃₅N₃O₄S
• Molecular Weight: 581.736
• Mol file: 765308-76-7.mol

Synonyms:p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside

Chemical Property of p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside

There total 5 articles about p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-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:

(2R,3S,4R,5S,6R)-5-Azido-2-hydroxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3,4-diol + benzyl bromide (100-39-0) → p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside (765308-76-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1021/jo049355h

Reference yield:

p-methylphenyl 2-deoxy-2-azido-3,4,6-tri-O-acetyl-1-thio-D-mannopyranoside (765308-75-6,501088-45-5) → p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside (765308-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 2.5 h / 0 - 20 °C

2: 4.61 g / NaH / dimethylformamide / 0 °C

With sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo049355h

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) → p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-2-azido-1-thio-D-mannopyranoside (765308-76-7)

Guidance literature:

Multi-step reaction with 5 steps

1: K₂CO₃; CuSO₄; TfN₃ / aq. methanol; CH₂Cl₂ / 48 h / 20 °C

2: 7.18 g / pyridine / 6 h / 0 - 20 °C

3: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 0 °C

4: NaOMe / methanol / 2.5 h / 0 - 20 °C

5: 4.61 g / NaH / dimethylformamide / 0 °C

With pyridine; triflic azide; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; potassium carbonate; copper(II) sulfate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo049355h

upstream raw materials:

benzyl bromide

p-methylphenyl 2-deoxy-2-azido-3,4,6-tri-O-acetyl-1-thio-D-mannopyranoside

D-mannosamine hydrochloride

2-azido-2-deoxy-D-mannopyranose

Downstream raw materials:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose