(1S,2S,3S,4R)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid

Base Information

• Chemical Name: (1S,2S,3S,4R)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid
• CAS No.: 123286-70-4
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.203

Synonyms:(1S,2S,3S,4R)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid

Chemical Property of (1S,2S,3S,4R)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4R)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid

There total 13 articles about (1S,2S,3S,4R)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid 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: 95.0%

(1R,2R,3R,4S)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid (R)-(+)-1-phenylethylamine salt → (1R,2R,3R,4S)-endo-3-(methoxycarbonyl)-bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid (4883-79-8,25925-29-5,36897-94-6,41527-42-8,96185-91-0,96243-73-1,96243-74-2,116404-46-7,123286-70-4,125226-91-7,131433-31-3,131433-32-4,142186-01-4,142186-02-5)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1002/chir.22404

Reference yield: 88.4%

dimethyl 5-cis-norbornene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1) → bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monomethyl ester (4883-79-8,25925-29-5,36897-94-6,41527-42-8,96185-91-0,96243-73-1,96243-74-2,116404-46-7,123286-70-4,125226-91-7,131433-31-3,131433-32-4,142186-01-4,142186-02-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1016/j.tetlet.2003.09.131

Reference yield:

methanol (67-56-1) + (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2) → bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monomethyl ester (4883-79-8,25925-29-5,36897-94-6,41527-42-8,96185-91-0,96243-73-1,96243-74-2,116404-46-7,123286-70-4,125226-91-7,131433-31-3,131433-32-4,142186-01-4,142186-02-5)

Guidance literature:

Rate constant; Heating; and with 10percent H₂O;

upstream raw materials:

methanol

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

dimethyl 5-cis-norbornene-2,3-dicarboxylate

dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Downstream raw materials:

5-endo-6-exo-dihydroxy-bicyclo-<2.2.1>heptane-2-exo-3-endo-dicarboxylic acid-γ-lactone

(2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid

(2S,3S)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid

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