(2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol
CAS No.:350483-13-5
Molecular Formula:C₂₁H₃₂O₅S₂
Molecular Weight:428.614
Hs Code.:

Synonyms:(2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol

There total 5 articles about (2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol 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%

: 350483-12-4
(Z)-7-Benzyloxy-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-4-methanesulfinyl-4-methylsulfanyl-hept-1-en-3-ol

: 350483-13-5
(2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1055/s-2001-13387

Reference yield:

: 175664-06-9
(2R,3S)-2-(2',2'-dibromovinyl)-3-(tert-butyldimethylsiloxy)-tetrahydropyran

: 350483-13-5
(2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: 89 percent / BuLi / tetrahydrofuran / 4 h / -78 - 0 °C

2.1: H₂; quinoline / Lindlar catalyst / ethanol / 28 h / 20 °C

3.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 0.75 h / -78 - 20 °C

4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

4.2: 85 percent / tetrahydrofuran / 1.5 h / -78 °C

5.1: 100 percent / TBAF / tetrahydrofuran / 5 h / 20 °C

With quinoline; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; 3.1: Swern oxidation;
DOI:10.1055/s-2001-13387

Reference yield:

: 349552-39-2
3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-2-yn-1-ol

: 350483-13-5
(2R,3S)-2-((Z)-7-Benzyloxy-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-hept-1-enyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂; quinoline / Lindlar catalyst / ethanol / 28 h / 20 °C

2.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 0.75 h / -78 - 20 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 5 h / 20 °C

With quinoline; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; 2.1: Swern oxidation;
DOI:10.1055/s-2001-13387