N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose

Base Information

• Chemical Name: N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose
• CAS No.: 1431388-86-1
• Molecular Formula: C₁₄H₁₅NO₅
• Molecular Weight: 277.277
• Mol file: 1431388-86-1.mol

Synonyms:N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose

Chemical Property of N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose

There total 8 articles about N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose 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:

C17H19NO5 → N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose (1431388-85-0) + N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose (1431388-86-1)

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide; In dichloromethane; at 20 ℃; for 12h; Overall yield = 98 %; Overall yield = 1.2 g; Inert atmosphere;

DOI:10.1016/j.tet.2013.03.074

Reference yield:

allyl N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-α-D-ribofuranoside (1431388-84-9) → N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose (1431388-85-0) + N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose (1431388-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 20 °C / Inert atmosphere

2: trimethylamine-N-oxide; osmium(VIII) oxide / dichloromethane / 12 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylamine-N-oxide; hydrogen; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2013.03.074

Reference yield:

allyl α-D-arabinofuranoside (103702-75-6,773896-71-2) → N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose (1431388-85-0) + N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-d-ribofuranose (1431388-86-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2.17 h / 0 - 20 °C / Inert atmosphere

2.1: sodium azide; ammonium chloride / ethanol; water / 48 h / Inert atmosphere; Reflux

3.1: pyridine / dichloromethane / 50 h / 0 - 20 °C / Inert atmosphere

4.1: triphenylphosphine / tetrahydrofuran; water / 20 h / 20 °C / Inert atmosphere

5.1: triethylamine / N,N-dimethyl-formamide / 20 h / 20 - 100 °C / Inert atmosphere

5.2: 4 h / 0 - 20 °C / Inert atmosphere

6.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 20 °C / Inert atmosphere

7.1: trimethylamine-N-oxide; osmium(VIII) oxide / dichloromethane / 12 h / 20 °C / Inert atmosphere

With pyridine; osmium(VIII) oxide; sodium azide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylamine-N-oxide; di-isopropyl azodicarboxylate; hydrogen; ammonium chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: |Staudinger Azide Reduction;

DOI:10.1016/j.tet.2013.03.074

upstream raw materials:

allyl 2,3-anhydro-5-O-benzoyl-α-D-lyxofuranoside

allyl 3-azido-5-O-benzoyl-3-deoxy-α-D-arabinofuranoside

allyl 3-azido-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-α-D-arabinofuranoside

allyl N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-α-D-ribofuranoside