(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

Base Information

Chemical Name:(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde
CAS No.:944943-12-8
Molecular Formula:C₂₉H₅₄O₅Si₂
Molecular Weight:538.916
Hs Code.:

Synonyms:(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

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Chemical Property of (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

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Technology Process of (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

There total 1 articles about (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde 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: 94.0%

: 944942-96-5
(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol

: 944943-12-8
(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol0710360

Reference yield: 84.0%

: 944943-12-8
(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

: 187324-67-0
(1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: 145412-54-0
dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane

: 944943-14-0
(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6S,8S)-3-hydroxy-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

Guidance literature:: (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; With triethylamine; In hexane; dichloromethane; at -78 ℃; for 1h;

(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde; In hexane; dichloromethane; at -78 - 20 ℃;

With methanol; dihydrogen peroxide; In hexane; dichloromethane; Further stages.;
DOI:10.1021/ol0710360

Reference yield:

: 944943-12-8
(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

: C₄₆H₇₈O₆Si₂

Guidance literature:: Multi-step reaction with 13 steps

1.1: triethylamine / CH₂Cl₂; hexane / 1 h / -78 °C

1.2: CH₂Cl₂; hexane / -78 - 20 °C

1.3: 84 percent / methanol; hydrogen peroxide / CH₂Cl₂; hexane

2.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

3.1: 80 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 3 h / -78 °C

4.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

5.1: 93 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / -10 - 0 °C

6.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.33 h / 20 °C / pH 7

7.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

8.1: 91 percent / CH₂Cl₂ / 72 h / 20 °C

9.1: 85 percent / potassium trimethylsilanolate / tetrahydrofuran / 9 h / 20 °C

10.1: 80 percent / triethylamine; 2,4,6-trichlorobenzoyl chloride; 4-(dimethylamino)pyridine / toluene / 1 h / 20 °C

11.1: 41 percent / trifluoroacetic acid / H₂O; tetrahydrofuran / 6 h / 20 °C

12.1: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

13.1: 40 percent / Grubbs' 2nd generation catalyst / CH₂Cl₂ / 72 h / Heating

With 2,6-dimethylpyridine; dmap; 2,4,6-trichlorobenzoyl chloride; potassium trimethylsilonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 4.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation;
DOI:10.1021/ol0710360