(2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione

Base Information

Chemical Name:(2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione
CAS No.:291313-57-0
Molecular Formula:C₁₈H₁₉NO₃
Molecular Weight:297.354
Hs Code.:

(2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0<sup>5,10</sup>]tridec-8-ene-7,13-dione

Synonyms:(2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione

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Chemical Property of (2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione

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Technology Process of (2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione

There total 7 articles about (2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione 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: 94.0%

: 210707-21-4
1-[(S)-2'-acetoxy-1'-benzylethyl]-1-azaspiro[4.5]deca-6,9-diene-2,8-dione

: 291313-57-0
(2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 2h;
DOI:10.1021/jo000341v

Reference yield:

: 3182-95-4
L-Phenylalaninol

: 291313-57-0
(2S,5S,10R)-2-benzyl-1-aza-4-oxatricyclo[8.3.0.0^5,10]tridec-8-ene-7,13-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: P,P-bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH₂Cl₂ / 0.5 h

1.2: 54 percent / Et₃N / CH₂Cl₂ / 10 h / 0 - 20 °C

2.1: 57 percent / aq. NaOH / 0.33 h

3.1: 74 percent / Burgess reagent / tetrahydrofuran / 2 h / Heating

4.1: 73 percent / potassium carbonate / methanol / 1 h / 20 °C

5.1: 50 percent Spectr_. / iodobenzene diacetate / 2,2,2-trifluoro-ethanol / 0.5 h / 25 °C

6.1: pyridine; 4-(dimethylamino)pyridine / 12 h / 20 °C

7.1: 94 percent / potassium carbonate / methanol / 2 h / 20 °C

With pyridine; dmap; Burgess Reagent; [bis(acetoxy)iodo]benzene; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; sodium hydroxide; dichloromethane; 2,2,2-trifluoroethanol; 1.1: coupling / 1.2: coupling / 2.1: Acetylation / 3.1: Cyclization / 4.1: Deacetylation / 5.1: Oxidation / 6.1: Acetylation / 7.1: Deacetylation;
DOI:10.1021/jo000341v