(-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one

Base Information

• Chemical Name: (-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one
• CAS No.: 756845-39-3
• Molecular Formula: C₂₈H₂₈N₂O₆S
• Molecular Weight: 520.606

Synonyms:(-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one

Chemical Property of (-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one

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Technology Process of (-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one

There total 2 articles about (-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one 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: 51.0%

(4R)-N-benzyloxycarbonyl-4-methanesulfonyloxy-L-prolyl chloride (756845-36-0) + (E)-N-benzylidenebenzylamine (27845-50-7) → (-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one (756845-39-3) + (+)-(3S,4R,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one (756845-41-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/jo049430o

Reference yield: 50.0%

(2S,4R)-4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (117811-87-7) + (E)-N-benzylidenebenzylamine (27845-50-7) → (-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one (756845-39-3) + (+)-(3S,4R,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one (756845-41-7)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In dichloromethane; optical yield given as %de; Reflux; Inert atmosphere;

DOI:10.1021/jo100061s

Reference yield: 98.0%

(-)-(3R,4S,7R)-2-benzyl-5-benzyloxycarbonyl-7-methanesulfonyloxy-3-phenyl-2,5-diazaspiro[3.4]octan-1-one (756845-39-3) → (-)-(3R,4S)-2-benzyl-5-benzyloxycarbonyl-3-phenyl-2,5-diazaspiro[3.4]oct-7-en-1-one

Guidance literature:

With potassium carbonate; In methanol; at 20 - 70 ℃; for 19h;

DOI:10.1021/jo049430o

upstream raw materials:

(4R)-N-benzyloxycarbonyl-4-methanesulfonyloxy-L-prolyl chloride

(E)-N-benzylidenebenzylamine

(2S,4R)-4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

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