(2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol

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Chemical Name:(2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol
CAS No.:910057-87-3
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:(2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol

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Chemical Property of (2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol

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Technology Process of (2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol

There total 8 articles about (2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-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: 79.0%

: 910057-86-2
2-{(E)-3-[(1S,2S)-2-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(3,3-dimethoxy-propyl)-butoxy]-allyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

: 910057-87-3
(2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol

Guidance literature:: With water; ytterbium(III) triflate; In acetonitrile; at 20 ℃;
DOI:10.1021/ol0614471

Reference yield:

: 910057-84-0
(S)-3-Benzyloxy-tetrahydro-furan-2-ol

: 910057-87-3
(2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 82 percent / MgBr₂*Et₂O; 1,2-dibromoethane / diethyl ether; CH₂Cl₂; tetrahydrofuran / 24 h / 20 °C

2.1: 93 percent / imidazole / CH₂Cl₂; toluene / 1 h / 20 °C

3.1: KH / tetrahydrofuran / -78 - 20 °C

3.2: 72 percent / MeLi / tetrahydrofuran; diethyl ether / 1.5 h / -78 - -40 °C

4.1: 70 percent / Cp₂ZrClH / CH₂Cl₂ / 24 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 12 h / -100 - 20 °C

6.1: 79 percent / Yb(OTf)3; H₂O / acetonitrile / 20 °C

With 1H-imidazole; Schwartz's reagent; n-butyllithium; water; potassium hydride; ethylene dibromide; magnesium bromide; ytterbium(III) triflate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ol0614471

Reference yield:

: 910057-96-4
(3S,4S)-3-Benzyloxy-7,7-dimethoxy-heptane-1,4-diol

: 910057-87-3
(2S,3R,6S)-6-[(S)-1'-benzyloxy-3'-hydroxy-propyl]-2-vinyl-tetrahydropyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / imidazole / CH₂Cl₂; toluene / 1 h / 20 °C

2.1: KH / tetrahydrofuran / -78 - 20 °C

2.2: 72 percent / MeLi / tetrahydrofuran; diethyl ether / 1.5 h / -78 - -40 °C

3.1: 70 percent / Cp₂ZrClH / CH₂Cl₂ / 24 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 12 h / -100 - 20 °C

5.1: 79 percent / Yb(OTf)3; H₂O / acetonitrile / 20 °C

With 1H-imidazole; Schwartz's reagent; n-butyllithium; water; potassium hydride; ytterbium(III) triflate; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ol0614471