(1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

Base Information

Chemical Name:(1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester
CAS No.:406682-77-7
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

Synonyms:(1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

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Chemical Property of (1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

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Technology Process of (1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

There total 1 articles about (1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester 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: 60.0%

: (1S,2R,3S,4R)-3-[2-(3-carboxy-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

: 406682-77-7
(1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

Guidance literature:: (1S,2R,3S,4R)-3-[2-(3-carboxy-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 2h;

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1002/jccs.200100132

Reference yield: 91.2%

: 406682-77-7
(1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

: 406682-79-9
(1S,2S,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 3h;
DOI:10.1002/jccs.200100132

Reference yield:

: 406682-77-7
(1S,2R,3S,4R)-3-[2-(3-formyl-7-oxabicyclo[2.2.1]hept-2-yl-methyl)phenyl]propionic acid methyl ester

: (1S,2S,3S,4R)-3-[2-(3-amino-7-oxabicyclo[2,2,1]hept-2-yl-methyl)phenyl]propionic acid hydrochloride

Guidance literature:: Multi-step reaction with 6 steps

1: 91.2 percent / NaOMe / methanol / 3 h / 20 °C

2: 65.9 percent / KMnO₄; 18-crown-6 / acetone / 2 h / 20 °C

3: ClCOOEt; Et₃N; NaN₃ / acetone

4: toluene / 3 h / Heating

5: 12 h / Heating

6: 5 percent aq. HCl

With hydrogenchloride; potassium permanganate; sodium azide; 18-crown-6 ether; sodium methylate; chloroformic acid ethyl ester; triethylamine; In methanol; acetone; toluene; 4: Curtius' rearrangement;
DOI:10.1002/jccs.200100132