methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate

Base Information

• Chemical Name: methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate
• CAS No.: 667917-81-9
• Molecular Formula: C₂₉H₃₁N₃O₇
• Molecular Weight: 533.581
• Mol file: 667917-81-9.mol

Synonyms:methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate

Chemical Property of methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate

There total 1 articles about methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate 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: 63.0%

(2S,3S,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-ethanesulfinyl-tetrahydro-pyran-2-carboxylic acid methyl ester → methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate (667917-81-9)

Guidance literature:

(2S,3S,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-ethanesulfinyl-tetrahydro-pyran-2-carboxylic acid methyl ester; With 2,6-di-tert-butyl-pyridine; trifluoromethylsulfonic anhydride; In diethyl ether; at -78 ℃; for 0.166667h;

With water; In diethyl ether; at -78 - 0 ℃; for 1h;

DOI:10.1021/jo0353029

Reference yield: 87.0%

methyl iodide (74-88-4) + methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate (667917-81-9) → methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-manno-hept-2-ulopyranosonate (667917-85-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo0353029

Reference yield:

methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-hept-2-ulopyranosonate (667917-81-9) → (3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate (667917-95-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / NaH / dimethylformamide / 2 h / 20 °C

2: pyridine; H₂S / H₂O / 16 h / 20 °C

3: pyridine / 20 h / 20 °C

4: 81 percent / NaBH₄ / tetrahydrofuran; ethanol / 20 h / 20 °C

5: 1H-tetrazole / CH₂Cl₂ / 5 h

6: tert-butyl hydroperoxide / CH₂Cl₂; decane / 20 °C

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; sodium tetrahydroborate; hydrogen sulfide; sodium hydride; In tetrahydrofuran; decane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0353029

Downstream raw materials:

methyl 3-azido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-manno-hept-2-ulopyranosonate

3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-manno-hept-2-ulopyranose

methyl 3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-manno-hept-2-ulopyranosonate

(3-acetamido-4,5,7-tri-O-benzyl-3-deoxy-2-O-methyl-α-D-mannno-hept-2-ulopyranos-1-yl) dibenzyl phosphate