(2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid

Base Information

• Chemical Name: (2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid
• CAS No.: 130464-52-7
• Molecular Formula: C₉H₁₂O₅
• Molecular Weight: 200.191

Synonyms:(2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid

Chemical Property of (2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid

Chemical Property:

Purity/Quality:

96% purity ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid

There total 3 articles about (2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-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: 100.0%

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) + methanol (67-56-1) → 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid monomethyl ester (57105-58-5,79315-91-6,104485-83-8,104485-84-9,112918-08-8,121423-53-8,130464-50-5,130464-52-7,135029-26-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; at 50 ℃; under 37503.8 Torr;

DOI:10.2174/157018011795906730

Reference yield:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → (2R,3S)-3-exo-methoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-exo-carboxylic acid (130464-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Rh/Al₂O₃ / ethyl acetate

2: quinine / toluene; CCl₄ / 60 h / -55 °C

With hydrogen; Quinine; Rh/Al₂O₃; In tetrachloromethane; ethyl acetate; toluene; 1: Catalytic hydrogenation / 2: Ring cleavage;

DOI:10.1021/jo000638t

Reference yield:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid monomethyl ester (57105-58-5,79315-91-6,104485-83-8,104485-84-9,112918-08-8,121423-53-8,130464-50-5,130464-52-7,135029-26-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C

2: Heating

With hydrogen; palladium on activated charcoal;

DOI:10.1021/ol0003735

upstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

methanol

Downstream raw materials:

methyl (1R,2S,3R,4S)-3-{[(benzyloxy)carbonyl]amino}-7-oxabicyclo[2.2.1]heptane-2-carboxylate

methyl (1R,2S,3R,4S)-3-[(4-fluoro-3-methylbenzyl)amino]-7-oxabicyclo[2.2.1]heptane-2-carboxylate

N-{3-[(1S,2R,7S,8R)-3-(4-fluoro-3-methylbenzyl)-6-hydroxy-4-oxo-11-oxa-3-aza-tricyclo[6.2.1.02,7]undec-5-en-5-yl]-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}methanesulfonamide

N-{3-[(1S,2R,7S,8R)-3-(4-fluoro-benzyl)-6-hydroxy-4-oxo-11-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-5-en-5-yl]-1-methyl-1-oxo-1λ⁶-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide

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