(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one
• CAS No.: 159063-89-5
• Molecular Formula: C₂₈H₂₉NO₅
• Molecular Weight: 459.542

Synonyms:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one

Chemical Property of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one

Chemical Property:

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Technology Process of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one

There total 15 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-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: 65.0%

(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (231618-90-9) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one (159063-89-5) + (2R,3R,4R,5R)-N-butyloxycarbonyl-2-(azidomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine (231618-91-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 35h;

DOI:10.1021/jo9902446

Reference yield: 11.0%

(2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-iodomethyl-pyrrolidine-1-carboxylic acid benzyl ester + triethyl phosphite (122-52-1) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one (159063-89-5) + (2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(diethoxy-phosphorylmethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

Heating;

DOI:10.1016/S0040-4039(97)10723-7

Reference yield:

benzyl [(2R,3R,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-yl]carbamate (160925-98-4) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidino<1,2-c>oxazole-3-one (159063-89-5)

Guidance literature:

With potassium chloride; mercury(II) diacetate; iodine; Multistep reaction;

DOI:10.1016/S0957-4166(00)86301-6

upstream raw materials:

mercury(II) diacetate

benzyl [(2R,3R,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-yl]carbamate

triethyl phosphite

(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(2R,3R,4R,5R)-2-(hydroxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine

(2R,3R,4R,5R)-N-butyloxycarbonyl-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-(hydroxymethyl)pyrrolidine

(2R,3R,4R,5R)-2-(acetamidomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine

(2R,3R,4R,5R)-N-methyl-2-(acetamidomethyl)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine

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