N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol

Base Information

• Chemical Name: N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol
• CAS No.: 868632-03-5
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.373
• Mol file: 868632-03-5.mol

Synonyms:N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol

Chemical Property of N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol

There total 1 articles about N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol 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: 70.0%

acetone (67-64-1) + N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol (679404-77-4) → N-benzyloxycarbonyl-1,5-dideoxy-2,3:4,6-di-O-isopropylidene-1,5-imino-D-mannitol + N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol (868632-03-5)

Guidance literature:

With pyridinium p-toluenesulfonate; at 20 ℃; for 14h;

DOI:10.1021/jo051454n

Reference yield:

N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol (868632-03-5) → 6-O-(5'-azidopentyl)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-4-O-methoxymethyl-D-mannitol (868632-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / imidazole / dimethylformamide / 0.03 h / 20 °C

2: 89 percent / diisopropylethylamine / CH₂Cl₂ / 19 h / 20 °C

3: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 50 h / 20 °C

4: 20 mg / CH₂Cl₂ / 18 h / high vacuum

With pyridine; 1H-imidazole; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051454n

Reference yield:

N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-D-mannitol (868632-03-5) → 6-O-(5'-azidopentyl)-1,5-dideoxy-1-[2-(N-phenylsulfonylindol-3-yl)ethyl]-1,5-imino-2,3-O-isopropylidene-4-O-methoxymethyl-D-mannitol (868632-13-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / imidazole / dimethylformamide / 0.03 h / 20 °C

2: 89 percent / diisopropylethylamine / CH₂Cl₂ / 19 h / 20 °C

3: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 50 h / 20 °C

4: 20 mg / CH₂Cl₂ / 18 h / high vacuum

5: 98 percent / KOH / ethanol / 15 h / Heating

6: 20 mg / NaH / CH₂Cl₂ / 16 h / 20 °C

With pyridine; 1H-imidazole; potassium hydroxide; sodium hydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051454n

upstream raw materials:

acetone

N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol

Downstream raw materials:

N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-4-O-methoxymethyl-D-mannitol

N-benzyloxycarbonyl-6-O-tert-butyldimethylsilyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-4-O-methoxymethyl-D-mannitol

6-O-(5'-azidopentyl)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-4-O-methoxymethyl-D-mannitol

6-O-(5'-azidopentyl)-1,5-dideoxy-1-[2-(N-phenylsulfonylindol-3-yl)ethyl]-1,5-imino-2,3-O-isopropylidene-4-O-methoxymethyl-D-mannitol