(R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol

Base Information

Chemical Name:(R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol
CAS No.:163228-64-6
Molecular Formula:C₁₆H₂₄O₅
Molecular Weight:296.364
Hs Code.:

Synonyms:(R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol

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Chemical Property of (R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol

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Technology Process of (R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol

There total 2 articles about (R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-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: 84.0%

: (2RS,4S,5S)-2-(4-methoxyphenyl)-5-methyl-4((R)-methylallyl)-[1,3]dioxane

: 163228-64-6
(R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; water; In acetone; at 25 ℃; for 20h;
DOI:10.1246/bcsj.68.967

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 163228-64-6
(R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / dl-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 25 °C

2: 84 percent / OsO₄, NMO, water / acetone / 20 h / 25 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; water; In dichloromethane; acetone;
DOI:10.1246/bcsj.68.967

Reference yield:

: 163228-64-6
(R)-3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butane-1,2-diol

: 163228-70-4
(2R,3S,4S,5S,6R)-3-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-oct-7-enal

Guidance literature:: Multi-step reaction with 5 steps

1: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

2: 1.) t-BuOK, n-BuLi, 2.) B-(-)-methoxydiisopinocampheylborane, 3.) BF₃*OEt₂, 4.) aq. H₂O₂, aq. NaOH

3: 92 percent / imidazole / dimethylformamide / 3 h / 50 °C

4: 98 percent / DIBAL / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 0.5 h

With 1H-imidazole; sodium hydroxide; sodium periodate; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.68.967