(1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester
CAS No.:172546-39-3
Molecular Formula:C₂₁H₂₁O₆P
Molecular Weight:400.368
Hs Code.:

Synonyms:(1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester

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Chemical Property of (1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester

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Technology Process of (1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester

There total 1 articles about (1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic 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: 85.0%

: 172721-74-3
(1R,2R,4S)-3-Oxo-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 172546-39-3
(1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran;
DOI:10.1016/0040-4039(95)01971-J

Reference yield:

: 172546-39-3
(1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester

: 511-59-1
(1S,2R,4R)-2-Methyl-3-methylene-2-(4-methyl-pent-3-enyl)-bicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / Pd(PPh₃)4 / 1,2-dichloro-ethane / 80 °C

2: 89 percent / DIBAH / CH₂Cl₂ / -78 °C

3: NaH / tetrahydrofuran / Ambient temperature

4: decahydronaphthalene / 150 °C

5: NaBH₄ / methanol

6: Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

7: dimethylsulfoxide

8: DIBAH / CH₂Cl₂ / -45 °C

9: n-BuLi / tetrahydrofuran / -30 °C

With dmap; sodium tetrahydroborate; n-butyllithium; sodium hydride; diisobutylaluminium hydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; decalin;
DOI:10.1016/0040-4039(95)01971-J

Reference yield:

: 172546-39-3
(1R,4S)-3-(Diphenoxy-phosphoryloxy)-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester

: 172546-40-6
(1R,4S)-2-(2-Benzenesulfinyl-ethoxymethyl)-3-methyl-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / Pd(PPh₃)4 / 1,2-dichloro-ethane / 80 °C

2: 89 percent / DIBAH / CH₂Cl₂ / -78 °C

3: NaH / tetrahydrofuran / Ambient temperature

With sodium hydride; diisobutylaluminium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1016/0040-4039(95)01971-J