[2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol

Base Information

Chemical Name:[2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol
CAS No.:440659-80-3
Molecular Formula:C₂₄H₄₄O₅Si
Molecular Weight:440.696
Hs Code.:

Synonyms:[2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol

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Chemical Property of [2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol

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Technology Process of [2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol

There total 1 articles about [2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-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: 88.0%

: 440103-90-2
(3R,4R,5R,6R,7R)-3,5,7-trimethyl-6-(p-methoxybenzyloxy)-4-((t-butyldimethylsilyl)oxy)-cyclohept-1-ene

: 440659-80-3
[2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol

Guidance literature:: (3R,4R,5R,6R,7R)-3,5,7-trimethyl-6-(p-methoxybenzyloxy)-4-((t-butyldimethylsilyl)oxy)-cyclohept-1-ene; With ozone; In methanol; dichloromethane; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - 20 ℃; for 3h; Further stages.;
DOI:10.1021/ol025872f

Reference yield:

: 440659-80-3
[2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol

: (2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-pentan-1-ol

Guidance literature:: With 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1021/ol025872f

Reference yield:

: 440659-80-3
[2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol

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

Guidance literature:: Multi-step reaction with 5 steps

1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 4 Angstroem molecular sieves / CH₂Cl₂ / 5 h / 20 °C

2: 2.9 g / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

3: 81 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 2.5 h / 20 - 60 °C

4: 84 percent / Bu₃SnH / AIBN / toluene / 2 h / Heating

5: N-methylmorpholine N-oxide; 4 Angstroem molecular sievs / tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

With dmap; 4 A molecular sieve; 4 Angstroem molecular sievs; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol025872f