2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione

Base Information

Chemical Name:2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione
CAS No.:191480-79-2
Molecular Formula:C₂₂H₂₁NO₄
Molecular Weight:363.413
Hs Code.:

Synonyms:2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione

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Chemical Property of 2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione

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Technology Process of 2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione

There total 8 articles about 2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-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: 96.0%

: 75-11-6
diiodomethane

: 191480-78-1
2-((1S,4S)-3-Benzyloxymethyl-4-hydroxy-cyclopent-2-enyl)-isoindole-1,3-dione

: 191480-79-2
2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione

Guidance literature:: With diethylzinc; In dichloromethane; at 0 ℃; for 10h;
DOI:10.1021/jo962124t

Reference yield:

: 85-44-9
phthalic anhydride

: 191480-79-2
2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / acetic anhydride / pyridine / 4 h / 90 °C

2: 90 percent / triethylamine trihydrofluoride / acetonitrile / Heating

3: 96 percent / Et₂Zn / CH₂Cl₂ / 10 h / 0 °C

With triethylamine trihydrofluoride; diethylzinc; acetic anhydride; In pyridine; dichloromethane; acetonitrile;
DOI:10.1021/jo962124t

Reference yield:

: 110567-21-0
(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene

: 191480-79-2
2-((1S,2S,4S,5R)-5-Benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 76 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

2: 87 percent / sodium azide / dimethylsulfoxide / Ambient temperature

3: 76 percent / sodium metaperiodate / methanol; H₂O / 36 h / Ambient temperature

4: 90 percent / triphenylphosphine / tetrahydrofuran; H₂O / 4 h / Heating

5: 77 percent / acetic anhydride / pyridine / 4 h / 90 °C

6: 90 percent / triethylamine trihydrofluoride / acetonitrile / Heating

7: 96 percent / Et₂Zn / CH₂Cl₂ / 10 h / 0 °C

With 1H-imidazole; sodium periodate; sodium azide; triethylamine trihydrofluoride; diethylzinc; acetic anhydride; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo962124t