3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose

Base Information

• Chemical Name: 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose
• CAS No.: 631918-82-6
• Molecular Formula: C₂₄H₃₃NO₁₀
• Molecular Weight: 495.527
• Mol file: 631918-82-6.mol

Synonyms:3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose

Chemical Property of 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose

There total 5 articles about 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose 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: 90.0%

benzyl chloroformate (501-53-1,94274-21-2) + 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose (631918-80-4) → 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose (631918-82-6)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; water; at 0 ℃; for 3h;

DOI:10.1016/S0968-0896(03)00231-1

Reference yield:

(1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate (329361-79-7) → 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose (631918-82-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / potassium carbonate / dimethylformamide / 20 h / 20 °C

2: 83 percent / LAH / tetrahydrofuran / 2 h / 20 °C

3: 82 percent / pyridine / 4 h / 0 - 20 °C

4: 71 percent / hydrogen / Pd/C / methanol / 12 h / 20 °C / 4137.18 Torr

5: 90 percent / NaHCO₃ / ethanol; H₂O / 3 h / 0 °C

With pyridine; lithium aluminium tetrahydride; hydrogen; sodium hydrogencarbonate; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00231-1

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-2-hydroxyethyl)amino-5,6-dideoxy-β-L-ido-heptofuranose (631918-76-8) → 3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose (631918-82-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / pyridine / 4 h / 0 - 20 °C

2: 71 percent / hydrogen / Pd/C / methanol / 12 h / 20 °C / 4137.18 Torr

3: 90 percent / NaHCO₃ / ethanol; H₂O / 3 h / 0 °C

With pyridine; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; ethanol; water;

DOI:10.1016/S0968-0896(03)00231-1

upstream raw materials:

benzyl chloroformate

3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose

(1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate

1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-2-hydroxyethyl)amino-5,6-dideoxy-β-L-ido-heptofuranose

Downstream raw materials:

1,2-O-isopropylidene-3,7-di-O-acetyl-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-5,6-dideoxy-β-L-ido-heptofuranose

(2S,3R,4R,5S)-1,2-Bis-(2-hydroxy-ethyl)-piperidine-3,4,5-triol