ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate

Base Information

• Chemical Name: ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate
• CAS No.: 870078-00-5
• Molecular Formula: C₂₆H₃₁NO₆
• Molecular Weight: 453.535
• Mol file: 870078-00-5.mol

Synonyms:ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate

Chemical Property of ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate

There total 2 articles about ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate 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%

(E)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-bromo-acrylic acid ethyl ester (57972-96-0,71536-59-9) + benzylamine (100-46-9) → ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate (870078-00-5)

Guidance literature:

In benzene; at 25 ℃; for 6h;

DOI:10.1039/b509216g

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate (870078-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / CH₂Cl₂ / 12 h / 25 °C

2: 70 percent / benzene / 6 h / 25 °C

In dichloromethane; benzene; 1: Wittig reaction;

DOI:10.1039/b509216g

Reference yield: 82.0%

ethyl 3-O-benzyl-5,6-N-benzyl-(E)-aziridine-1,2-O-isopropylidenehept-5,6-dideoxy-β-L-ido-heptofuranuronate (870078-00-5) → ethyl 3-O-benzyl-5-(N-benzyl)amino-1,2-O-isopropylidene-β-L-glycero-L-ido-heptofuranuronate (870078-01-6)

Guidance literature:

With trifluoroacetic acid; In acetone; at 25 ℃; for 24h;

DOI:10.1039/b509216g

upstream raw materials:

(E)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-bromo-acrylic acid ethyl ester

benzylamine

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

ethyl 3-O-benzyl-5-(N-benzyl)amino-1,2-O-isopropylidene-β-L-glycero-L-ido-heptofuranuronate

6-aldehydo-5-(N-benzyl-N-benzoxycarbonyl)amino-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-ido-hexo-1,4-furanose

5-(N-benzoxycarbonyl)amino-3,6,7-trihydroxy-5-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-hepto-1,4-furanose

3,6,7-tri-O-acetyl-5-(N-benzoxycarbonylamino)-5-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-heptofuranose