N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

Base Information

Chemical Name:N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester
CAS No.:1451369-78-0
Molecular Formula:C₃₁H₃₅NO₁₂
Molecular Weight:613.618
Hs Code.:

Synonyms:N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

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Chemical Property of N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

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Technology Process of N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

There total 5 articles about N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester 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:

: 1451369-68-8
N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

: 1451369-78-0
N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridine*THF; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

1.2: DOWEX? 50WX2 / 1 h / 20 °C

2.1: pyridine / 0 - 20 °C

With pyridine; pyridine*THF; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1039/c3ob41212a

Reference yield:

: C₂₅H₂₉NO₉

: 108-24-7
acetic anhydride

: 1451369-78-0
N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

Guidance literature:: With pyridine; at 0 - 20 ℃;
DOI:10.1039/c3ob41212a

Reference yield:

: 1451369-72-4
4-methylphenyl 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside

: 1451369-78-0
N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 16 h / 20 °C / Molecular sieve; Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 48 h / 40 °C

3.3: 0.5 h / 0 °C

4.1: pyridine*THF; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

4.2: DOWEX? 50WX2 / 1 h / 20 °C

5.1: pyridine / 0 - 20 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; pyridine*THF; tetrabutyl ammonium fluoride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1039/c3ob41212a