(2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine

Base Information

• Chemical Name: (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine
• CAS No.: 1333524-01-8
• Molecular Formula: C₅₄H₅₁NO₁₈
• Molecular Weight: 1001.99
• Mol file: 1333524-01-8.mol

Synonyms:

Chemical Property of (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine

There total 10 articles about (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine 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:

(2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-([2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy]methyl)pyrrolidine (1333523-86-6) → (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine (1333524-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 1 h / 20 °C

2: trifluoroacetic acid / 0.17 h / 0 - 20 °C

With pyridine; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/c1cc13675e

Reference yield:

(2S,3S,4S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine (1333523-78-6) → (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine (1333524-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dichloromethane / 0.5 h / -40 °C / Molecular sieve; Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere; Molecular sieve

2.1: pyridine / dichloromethane / 1 h / 20 °C

3.1: trifluoroacetic acid / 0.17 h / 0 - 20 °C

With pyridine; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/c1cc13675e

Reference yield:

benzyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranoside (1333523-96-8) → (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine (1333524-01-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 24 h

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C

3.1: dichloromethane / 0.5 h / -40 °C / Molecular sieve; Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere; Molecular sieve

4.1: pyridine / dichloromethane / 1 h / 20 °C

5.1: trifluoroacetic acid / 0.17 h / 0 - 20 °C

With pyridine; palladium 10% on activated carbon; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;

DOI:10.1039/c1cc13675e

upstream raw materials:

(2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-([2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy]methyl)pyrrolidine

(2S,3S,4S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine

benzyl α-L-arabinofuranoside

benzyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-α-L-arabinofuranoside