(2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol

Base Information

Chemical Name:(2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol
CAS No.:179238-95-0
Molecular Formula:C₁₅H₂₂O₃S
Molecular Weight:282.404
Hs Code.:

Synonyms:(2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol

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Chemical Property of (2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol

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Technology Process of (2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol

There total 5 articles about (2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol 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: 82.0%

: 179238-94-9
(2S,3R)-4-Benzyl-3-[3-hydroxy-2-methyl-1-oxo-3-[(4-phenylsulfanyl)-3,4,5,6-tetrahydro-(2H)-pyran-4-yl]propionyl]oxazolidin-2-one

: 179238-95-0
(2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 4h;
DOI:10.1039/b001893g

Reference yield:

: 13865-50-4
methoxymethyl phenyl sulfide

: 179238-95-0
(2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 78 percent / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.1: 74 percent / SOCl₂; Et₃N / CH₂Cl₂ / 0.75 h

3.1: Et₂AlCl / CH₂Cl₂; hexane / 5 h / -88 °C

3.2: 0.58 g / aq. H₂O₂ / CH₂Cl₂; methanol; hexane / 1 h / -88 - 0 °C

4.1: 82 percent / aq. LiBH₄ / tetrahydrofuran; diethyl ether / 4 h / 0 °C

With lithium borohydride; n-butyllithium; thionyl chloride; diethylaluminium chloride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Rearrangement / 3.1: Addition / 3.2: Oxidation / 4.1: Hydrolysis;
DOI:10.1039/b001893g

Reference yield:

: 179088-48-3
4-(Phenylsulfanyl)-3,4,5,6-tetrahydropyran-4(2H)-carboxaldehyde

: 179238-95-0
(2S,3R)-2-Methyl-1-(4-phenylsulfanyl-3,4,5,6-tetrahydro-(2H)-pyran-4-yl)propane-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: Et₂AlCl / CH₂Cl₂; hexane / 5 h / -88 °C

1.2: 0.58 g / aq. H₂O₂ / CH₂Cl₂; methanol; hexane / 1 h / -88 - 0 °C

2.1: 82 percent / aq. LiBH₄ / tetrahydrofuran; diethyl ether / 4 h / 0 °C

With lithium borohydride; diethylaluminium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Addition / 1.2: Oxidation / 2.1: Hydrolysis;
DOI:10.1039/b001893g