(2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran

Base Information

Chemical Name:(2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran
CAS No.:952609-45-9
Molecular Formula:C₂₂H₂₆O₅S
Molecular Weight:402.511
Hs Code.:

Synonyms:(2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran

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Chemical Property of (2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran

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Technology Process of (2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran

There total 8 articles about (2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran 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: 86.0%

: 952609-46-0
C₂₂H₂₈O₆S

: 952609-45-9
(2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2007.06.110

Reference yield:

: 952609-40-4
(2R,3S)-3-methoxy-hex-5-ene-1,2-diol

: 952609-45-9
(2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 65 percent / K₂CO₃; TBAI / acetone / 18 h / Heating

2.1: 71 percent / m-chloroperbenzoic acid / CHCl₃; H₂O / 6 h / 20 °C

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

4.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.33 h / -78 °C

4.2: 71 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: 86 percent / methanesulfonyl chloride; triethylamine / CH₂Cl₂ / 2 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetone; 3.1: Swern oxidation;
DOI:10.1016/j.tet.2007.06.110

Reference yield:

: 942505-94-4
(S)-1-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-but-3-enyl methyl ether

: 952609-45-9
(2R,3S)-2-(benzyloxymethyl)-3-methoxy-5-[(E)-2-(4-methylphenylsulfonyl)-ethenyl]-tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1.1: 81 percent / acetic acid; water / 6 h / 20 °C

2.1: 65 percent / K₂CO₃; TBAI / acetone / 18 h / Heating

3.1: 71 percent / m-chloroperbenzoic acid / CHCl₃; H₂O / 6 h / 20 °C

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

5.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.33 h / -78 °C

5.2: 71 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.1: 86 percent / methanesulfonyl chloride; triethylamine / CH₂Cl₂ / 2 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; water; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetone; 4.1: Swern oxidation;
DOI:10.1016/j.tet.2007.06.110