benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate

Base Information

• Chemical Name: benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate
• CAS No.: 107699-40-1
• Molecular Formula: C₂₇H₂₉NO₆
• Molecular Weight: 463.53

Synonyms:benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate

Chemical Property of benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate

Chemical Property:

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Technology Process of benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate

There total 1 articles about benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate 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:

benzyl bromide (100-39-0) + (3R*,3aR*,6S*,7aR*)-6-acetoxymethyl-3-p-methoxyphenyl-4-oxo-2-phenyl-tetrahydropyrano-<3,4-d>-isoxazolidine (102972-08-7) → benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate (107699-40-1)

Guidance literature:

With potassium hydroxide; 18-crown-6 ether; Yield given. Multistep reaction; 1.) dioxane, RT, overnight, 2.) DMF,;

Reference yield: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate (107699-40-1) → benzyl (3R*,4R*,5R*,2'S*)-5-<2',3'-di(tert-butyldimethylsilyloxy)propyl>-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate (107699-41-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

Reference yield: 85.0%

benzyl (3R*,4R*,5R*,2'S*)-5-(2',3'-dihydroxypropyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate (107699-40-1) → benzyl (3R*,4R*,5R*)-5-(2'-oxoethyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate (107699-44-5)

Guidance literature:

With sodium periodate; In water; for 48h; Ambient temperature;

upstream raw materials:

benzyl bromide

(3R*,3aR*,6S*,7aR*)-6-acetoxymethyl-3-p-methoxyphenyl-4-oxo-2-phenyl-tetrahydropyrano-<3,4-d>-isoxazolidine

Downstream raw materials:

benzyl (3R*,4R*,5R*,2'S*)-5-<2',3'-di(tert-butyldimethylsilyloxy)propyl>-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate

benzyl (3R*,4R*,5R*)-5-(2'-oxoethyl)-3-p-methoxyphenyl-2-phenylisoxazolidine-4-carboxylate

(3R*,4R*)-3-<(1'R*)-1',3'-dihydroxypropyl>-4-p-methoxyphenyl-1-phenylazetidinone-2

(3R*,4R*)-3-<(1'R*)-1'-hydroxy-3'-tert-butyldimethylsilyloxypropyl>-4-p-methoxyphenyl-1-phenylazetidinone-2

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