methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate

Base Information

• Chemical Name: methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate
• CAS No.: 1623755-85-0
• Molecular Formula: C₃₇H₅₂O₇SeSi
• Molecular Weight: 715.861

Synonyms:methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate

Chemical Property of methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate

Chemical Property:

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Technology Process of methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate

There total 6 articles about methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate 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: 90.0%

(5S)-5-(2-methylallyl)-3-(phenylselanyl)dihydrofuran-2(3H)-one (1376854-00-0) + methyl-2-((1S,2R,3S)-2-(2-oxoethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate (1623755-16-7) → methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate (1623755-85-0)

Guidance literature:

(5S)-5-(2-methylallyl)-3-(phenylselanyl)dihydrofuran-2(3H)-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 - -10 ℃; for 1h; Inert atmosphere;

methyl-2-((1S,2R,3S)-2-(2-oxoethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate; In tetrahydrofuran; for 1h; Inert atmosphere;

DOI:10.1002/anie.201400617

Reference yield:

methyl-6-((ethoxycarbonyl)oxy)-2-((1S,2R,3S)-2-(2-((4-methoxyphenyl)diphenylmethoxy)ethyl)-3-((triisopropylsilyl)oxy)cyclobutanecarbonyl)hex-4-ynoate → methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate (1623755-85-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Inert atmosphere; Reflux

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1 h / -78 - -10 °C / Inert atmosphere

3.2: 1 h / Inert atmosphere

With n-butyllithium; pyridinium p-toluenesulfonate; diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1002/anie.201400617

Reference yield:

methyl-2-((1S,2R,3S)-2-(2-hydroxyethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate (1623755-81-6) → methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate (1623755-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Inert atmosphere; Reflux

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1 h / -78 - -10 °C / Inert atmosphere

2.2: 1 h / Inert atmosphere

With n-butyllithium; diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethyl acetate;

DOI:10.1002/anie.201400617

upstream raw materials:

methyl-2-((1S,2R,3S)-2-(2-hydroxyethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate

(5S)-5-(2-methylallyl)-3-(phenylselanyl)dihydrofuran-2(3H)-one

methyl-2-((1S,2R,3S)-2-(2-oxoethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate

2-(phenylselanyl)acetic acid

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