(1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester

Base Information

• Chemical Name: (1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester
• CAS No.: 1380681-55-9
• Molecular Formula: C₃₈H₃₄O₉
• Molecular Weight: 634.683

Synonyms:(1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester

Chemical Property of (1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester

There total 11 articles about (1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl 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: 72.0%

(1R,2S,3R,4S,5S)-5-benzoyloxymethyl-1-hydroxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester (1380681-54-8) + benzoyl chloride (98-88-4) → (1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester (1380681-55-9)

Guidance literature:

With 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.1002/asia.201200077

Reference yield:

4-bromo-2-furancarbaldehyde (21921-76-6) → (1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester (1380681-55-9)

Guidance literature:

Multi-step reaction with 11 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

With 1H-imidazole; 1-methyl-1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; trisylhydrazine; boron trifluoride diethyl etherate; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 6.1: Diels-Alder reaction;

DOI:10.1002/asia.201200077

Reference yield:

4-bromo-2-tert-butyldimethylsilyloxymethylfuran (913828-41-8) → (1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dibenzyl ester (1380681-55-9)

Guidance literature:

Multi-step reaction with 9 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

With 1-methyl-1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; trisylhydrazine; boron trifluoride diethyl etherate; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; chloroform; isopropyl alcohol; toluene; acetonitrile; 4.1: Diels-Alder reaction;

DOI:10.1002/asia.201200077

upstream raw materials:

4-bromo-2-furancarbaldehyde

4-bromo-2-tert-butyldimethylsilyloxymethylfuran

4-benzoyloxymethyl-2-tert-butyldimethylsiloxymethylfuran

5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-furaldehyde

Downstream raw materials:

(1R,2S,3R,4S,5S)-1,5-bisbenzoyloxymethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dimethyl ester

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