N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

Base Information

Chemical Name:N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester
CAS No.:1451369-69-9
Molecular Formula:C₄₈H₆₃NO₁₀Si₂
Molecular Weight:870.2
Hs Code.:

Synonyms:N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

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Chemical Property of N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

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Technology Process of N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

There total 2 articles about N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-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: 82.0%

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

: 939-26-4
2-bromomethylnaphthyl bromide

: 1451369-69-9
N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-d₆-formamide; at -20 ℃; for 6h;
DOI:10.1002/anie.201404904

Reference yield:

: 1451369-66-6
4-methylphenyl 2-O-(2-naphthyl)methyl-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside

: 13504-85-3
(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

: 1451369-69-9
N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

: 1451369-93-9
N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

Guidance literature:: 4-methylphenyl 2-O-(2-naphthyl)methyl-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside; (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -40 - 20 ℃; for 0.25h; Overall yield = 76 %; Overall yield = 265 mg; Inert atmosphere;
DOI:10.1039/c3ob41212a

Reference yield:

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

: 1451369-69-9
N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-2-O-(2-naphthyl)methyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester

: C₇₂H₁₀₃NO₁₅SSi₄

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; at 20 ℃; Molecular sieve;
DOI:10.1002/anie.201404904