methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate

Base Information

• Chemical Name: methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate
• CAS No.: 168960-60-9
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331

Synonyms:methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate

Chemical Property of methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate

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Technology Process of methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate

There total 2 articles about methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate 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: 64.0%

Benzoic acid (E)-(2S,3S,5R)-3,5-dihydroxy-2-iodo-7-methoxycarbonyl-hept-6-enyl ester → (1R,5S,6S,7S)-6-benzoyloxymethyl-7-hydroxy-2-oxabicyclo<3.2.0>octan-3-one + (1R,5S,6R,7S)-6-benzoyloxymethyl-7-hydroxy-2-ocabicyclo<3.2.0>octaan-3-one (168960-59-6) + methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate (168960-60-9) + methyl (1S,2R,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydrocyclopentyl)ethanoate

Guidance literature:

With air; triethyl borane; tri-n-butyl-tin hydride; In hexane; xylene; at 20 ℃; for 0.166667h;

DOI:10.1039/a904206g

Reference yield: 64.0%

Benzoic acid (E)-(2R,3S,5R)-3,5-dihydroxy-2-iodo-7-methoxycarbonyl-hept-6-enyl ester → (1R,5S,6S,7S)-6-benzoyloxymethyl-7-hydroxy-2-oxabicyclo<3.2.0>octan-3-one + (1R,5S,6R,7S)-6-benzoyloxymethyl-7-hydroxy-2-ocabicyclo<3.2.0>octaan-3-one (168960-59-6) + methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate (168960-60-9) + methyl (1S,2R,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydrocyclopentyl)ethanoate

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In xylene; for 0.25h; Ambient temperature;

Reference yield: 89.0%

triethylsilyl chloride (994-30-9) + methyl (1S,2S,3R,4R)-2-(2-benzoyloxymethyl-3,5-dihydroxycyclopentyl)ethanoate (168960-60-9) → Benzoic acid (1R,2R,3R,5S)-2-methoxycarbonylmethyl-3,5-bis-triethylsilanyloxy-cyclopentylmethyl ester

Guidance literature:

With pyridine; at 60 ℃; for 0.25h;

DOI:10.1039/a904206g

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