(2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol

Base Information

• Chemical Name: (2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol
• CAS No.: 1357516-70-1
• Molecular Formula: C₃₄H₃₄N₃O₂P
• Molecular Weight: 547.637

Synonyms:(2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol

Chemical Property of (2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol

Chemical Property:

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Technology Process of (2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol

There total 2 articles about (2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol 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: 88.0%

(2R,3S,4R,5S)-5-azidomethyl-1-N-benzyl-2-cyano-3,4-dihydroxy-3,4-O-isopropylidenepyrrolidine (1147545-67-2) + triphenylphosphine (603-35-0) → (2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol (1357516-70-1)

Guidance literature:

With magnesium bromide ethyl etherate; In tetrahydrofuran; dichloromethane; at 20 ℃; for 5.5h;

DOI:10.1016/j.tet.2011.12.024

Reference yield: 71.0%

(2R,3S,4R,5S)-5-azidomethyl-1-N-benzyl-2-cyano-3,4-dihydroxy-3,4-O-isopropylidenepyrrolidine (1147545-67-2) + triphenylphosphine (603-35-0) → (2R,3S,4R,5S)-5-(aminomethyl)-1-benzyl-2-cyano-3,4-O-isopropylidenepyrrolidine-3,4-diol (1357516-68-7) + (2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol (1357516-70-1)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran;

DOI:10.1016/j.tet.2011.12.024

Reference yield: 99.0%

(2R,3S,4R,5S)-1-benzyl-2-cyano-3,4-O-isopropylidene-5-(((triphenylphosphoranylidene)amino)methyl)pyrrolidine-3,4-diol (1357516-70-1) → (2R,3S,4R,5S)-5-(aminomethyl)-1-benzyl-2-cyano-3,4-O-isopropylidenepyrrolidine-3,4-diol (1357516-68-7)

Guidance literature:

With methanol; ammonia;

DOI:10.1016/j.tet.2011.12.024

upstream raw materials:

(2R,3S,4R,5S)-5-azidomethyl-1-N-benzyl-2-cyano-3,4-dihydroxy-3,4-O-isopropylidenepyrrolidine

triphenylphosphine

Downstream raw materials:

(2R,3S,4R,5S)-5-(aminomethyl)-1-benzyl-2-cyano-3,4-O-isopropylidenepyrrolidine-3,4-diol

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