(1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

Base Information

Chemical Name:(1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol
CAS No.:538334-76-8
Molecular Formula:C₃₄H₄₈O₅Si₂
Molecular Weight:592.923
Hs Code.:

Synonyms:(1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

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Chemical Property of (1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

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Technology Process of (1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

There total 6 articles about (1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-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:

: 538334-73-5
(2R,3S,4R,5R)-4,5-dibenzyloxy-3-(tert-butyldimethylsilyloxy)-2-(dimethylphenylsilanyl)cyclohexene

: 538334-77-9
(1S,2R,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

: 538334-76-8
(1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

Guidance literature:: With Quinuclidine; potassium osmate(VI); methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 23 ℃; for 12h;
DOI:10.1021/ol034349d

Reference yield:

: 535994-37-7
(2S,3R)-2,3-dibenzyloxy-4-penten-1-al

: 538334-76-8
(1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: BF₃*OEt₂ / tetrahydrofuran / 16 h / -78 - 23 °C

1.2: 30 percent H₂O₂ / tetrahydrofuran; H₂O / 2 h / 23 °C / pH 7

2.1: 87 percent / [N,N'-(Mes)2imidazolidin-2-yl]Ru=CHPh(PCy₃)Cl₂ / toluene / 2 h / 80 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 0 °C

4.1: MeSO₂NH₂; quinuclidine; K₂OsO₄*H₂O / K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 12 h / 23 °C

With Quinuclidine; 2,6-dimethylpyridine; potassium osmate(VI); methanesulfonamide; boron trifluoride diethyl etherate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1021/ol034349d

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 538334-76-8
(1R,2S,3R,4S,5S,6R)-5,6-dibenzyloxy-4-(tert-butyldimethylsilyloxy)-3-(dimethylphenylsilanyl)cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 0 °C

2: MeSO₂NH₂; quinuclidine; K₂OsO₄*H₂O / K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 12 h / 23 °C

With Quinuclidine; 2,6-dimethylpyridine; potassium osmate(VI); methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol034349d