(1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

Base Information

Chemical Name:(1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride
CAS No.:1380681-72-0
Molecular Formula:C₁₉H₁₈O₈
Molecular Weight:374.347
Hs Code.:

Synonyms:

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Chemical Property of (1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

Chemical Property:

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Technology Process of (1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

There total 13 articles about (1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride 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:

: 21921-76-6
4-bromo-2-furancarbaldehyde

: 1380681-72-0
(1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium tetrahydroborate / methanol / 10 h / 0 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / diethyl ether; hexane; toluene / 1 h / -70 - -40 °C / Inert atmosphere

3.2: 3 h / -70 - 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 12 h / 0 - 20 °C

5.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

6.1: dichloromethane / 20 °C / 5250530 Torr

7.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 °C / Inert atmosphere

7.2: 24 h / 0 - 20 °C / Inert atmosphere

8.1: trisylhydrazine / 1,2-dimethoxyethane / 5 h / 50 °C

9.1: boron trifluoride diethyl etherate / acetonitrile / 1 h / 0 °C

10.1: CHIRALPAK_.(R). IA / hexane; chloroform; isopropyl alcohol

11.1: 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C

12.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C

13.1: acetic anhydride / 4 h / 50 °C

With 1H-imidazole; 1-methyl-1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; trisylhydrazine; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 6.1: Diels-Alder reaction;
DOI:10.1002/asia.201200077

Reference yield:

: C₁₉H₂₀O₉

: 1380681-72-0
(1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

Guidance literature:: With acetic anhydride; at 50 ℃; for 4h;
DOI:10.1002/asia.201200077

Reference yield:

: 913828-41-8
4-bromo-2-tert-butyldimethylsilyloxymethylfuran

: 1380681-72-0
(1S,2R,3S,4R,5R)-1-acetoxymethyl-5-benzoyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

Guidance literature:: Multi-step reaction with 11 steps

1.1: n-butyllithium / diethyl ether; hexane; toluene / 1 h / -70 - -40 °C / Inert atmosphere

1.2: 3 h / -70 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 12 h / 0 - 20 °C

3.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

4.1: dichloromethane / 20 °C / 5250530 Torr

5.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 °C / Inert atmosphere

5.2: 24 h / 0 - 20 °C / Inert atmosphere

6.1: trisylhydrazine / 1,2-dimethoxyethane / 5 h / 50 °C

7.1: boron trifluoride diethyl etherate / acetonitrile / 1 h / 0 °C

8.1: CHIRALPAK_.(R). IA / hexane; chloroform; isopropyl alcohol

9.1: 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C

10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C

11.1: acetic anhydride / 4 h / 50 °C

With 1-methyl-1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; trisylhydrazine; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; chloroform; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; 4.1: Diels-Alder reaction;
DOI:10.1002/asia.201200077