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

Base Information

• Chemical Name: (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine
• CAS No.: 1333523-84-4
• Molecular Formula: C₃₆H₃₉NO₁₂
• Molecular Weight: 677.705
• Mol file: 1333523-84-4.mol

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

Chemical Property of (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-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-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine

There total 3 articles about (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-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: 63.0%

(2S,3S,4S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine (1333523-78-6) + 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate (251451-05-5) → (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine (1333523-84-4)

Guidance literature:

(2S,3S,4S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine; 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate; In dichloromethane; at -40 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c1cc13675e

Reference yield:

(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (52019-89-3,97058-12-3,98632-49-6,100937-51-7,100937-52-8,100937-53-9,105990-40-7,105990-41-8,105990-42-9,129568-47-4,186759-56-8,187339-50-0) → (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine (1333523-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / methanol / 4 h / 20 °C

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

2.2: 1 h / 0 °C / Inert atmosphere; Molecular sieve

With triethylamine; In methanol; dichloromethane;

DOI:10.1039/c1cc13675e

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine (1333523-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / methanol / 4 h / 20 °C

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

2.2: 1 h / 0 °C / Inert atmosphere; Molecular sieve

With triethylamine; In methanol; dichloromethane;

DOI:10.1039/c1cc13675e

upstream raw materials:

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

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl 2,2,2-trichloroacetimidate

di-tert-butyl dicarbonate

(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol

Downstream raw materials:

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