(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene

Base Information

Chemical Name:(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene
CAS No.:322428-55-7
Molecular Formula:C₂₀H₃₀O₅
Molecular Weight:350.455
Hs Code.:

Synonyms:(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene

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Chemical Property of (3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene

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Technology Process of (3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene

There total 6 articles about (3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene 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: 72.0%

: 322428-96-6
(R)-2-Methoxy-3-[(2R,4R,6R)-6-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-propionaldehyde

: 322428-55-7
(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene

Guidance literature:: In tetrahydrofuran; toluene; at -78 - 0 ℃;
DOI:10.1021/ol000305i

Reference yield:

: 322428-47-7
(4S)-5-[(4R,6R)-4-((E)-2-phenylethenyl)-2,2-dimethyl-1,3-dioxan-6-yl]-4-p-methoxybenzyloxy-2-pentene

: 322428-55-7
(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 77 percent / O₂; PdCl₂; Cu(OAc)2*H₂O / N,N-dimethyl-acetamide; H₂O / 19.5 h / 20 °C

2.1: 85 percent / PPTS / methanol / 6.5 h

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: 98 percent / tetrahydrofuran / 14.67 h / 0 - 20 °C

4.1: OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

5.1: NaIO₄; sodium phosphate / tetrahydrofuran; H₂O / 0.42 h / 0 - 20 °C / pH 7

6.1: 134 mg / tetrahydrofuran; toluene / 0.2 h / -78 - 0 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; copper diacetate; oxygen; pyridinium p-toluenesulfonate; sodium hydride; sodium phosphate; palladium dichloride; In tetrahydrofuran; methanol; N,N-dimethyl acetamide; water; acetone; toluene; tert-butyl alcohol; 1.1: Wacker oxidation / 6.1: Tebbe olefination;
DOI:10.1016/S0040-4020(01)00593-2

Reference yield:

: 322428-33-1
(4R)-5-[(4R,6R)-4-((E)-2-phenylethenyl)-2,2-dimethyl-1,3-dioxan-6-yl]-4-p-methoxybenzyloxy-2-pentanone

: 322428-55-7
(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyl-tetrahydropyran-6-yl]-3-hydroxy-1-butene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent / PPTS / methanol / 6.5 h

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 98 percent / tetrahydrofuran / 14.67 h / 0 - 20 °C

3.1: OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

4.1: NaIO₄; sodium phosphate / tetrahydrofuran; H₂O / 0.42 h / 0 - 20 °C / pH 7

5.1: 134 mg / tetrahydrofuran; toluene / 0.2 h / -78 - 0 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; pyridinium p-toluenesulfonate; sodium hydride; sodium phosphate; In tetrahydrofuran; methanol; water; acetone; toluene; tert-butyl alcohol; 5.1: Tebbe olefination;
DOI:10.1016/S0040-4020(01)00593-2