(2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

Base Information

Chemical Name:(2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane
CAS No.:848565-50-4
Molecular Formula:C₂₃H₄₀O₈SSi
Molecular Weight:504.717
Hs Code.:

Synonyms:(2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

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Chemical Property of (2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

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Technology Process of (2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

There total 2 articles about (2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane 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: 99.0%

: 98-59-9
p-toluenesulfonyl chloride

: 241811-67-6
(2R,3R,5S,6S)-[3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxan-2-yl]methanol

: 848565-50-4
(2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1002/anie.200462264

Reference yield:

: 241811-66-5
(2R,3R,5S,6S)-(3-hydroxymethyl-5,6-dimethoxy-5,6-dimethyl[1,4]dioxan-2-yl)methanol

: 848565-50-4
(2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 20 °C

2: dmap; pyridine / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium hydride; In tetrahydrofuran;
DOI:10.1016/j.tetasy.2012.08.008

Reference yield:

: 848565-50-4
(2R,3R,5S,6S)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

: C₄₆H₆₂O₁₇S₂

Guidance literature:: Multi-step reaction with 5 steps

1.1: 84 percent / CuBr / diethyl ether / 8 h / 0 °C

2.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 0 °C

3.1: 69 percent / potassium hexamethyldisilazide / tetrahydrofuran / 5 h / -78 - 0 °C

4.1: 99 percent / second generation Grubbs catalyst / CH₂Cl₂ / 1 h / Heating

5.1: Ad-mix-α; MeSO2NH2; NaHCO3 / 2-methyl-propan-2-ol / 96 h / 0 °C

5.2: pyridine / 20 h / 0 - 20 °C

With AD-mix-α; methanesulfonamide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; copper(I) bromide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.1002/anie.200462264