2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester
CAS No.:439217-28-4
Molecular Formula:C₂₄H₄₂O₄Si
Molecular Weight:422.681
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester

There total 8 articles about 2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester 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: 95.0%

: 994-30-9
triethylsilyl chloride

: 439217-33-1
2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-5-hydroxy-2-methyl-pentyl ester

: 439217-28-4
2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1021/ol026034o

Reference yield:

: 147649-95-4
(S)-2-Methyl-4-pentenoic acid phenylmethyl ester

: 439217-28-4
2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: AD mix α; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 22.5 h / 0 - 5 °C

2: 42 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

3: 99 percent / lithium borohydride / methanol; tetrahydrofuran / 4 h / 0 °C

4: 66 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

5: sodium hydride / dimethylformamide / -50 - -10 °C

6: 340 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h

7: 95 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

With 2,6-dimethylpyridine; dmap; AD-mix-α; lithium borohydride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ol026034o

Reference yield:

: 175272-36-3
(4R)-4-Benzyl-3-[(2S)-2-methyl-4-pentenoyl]-1,3-oxazolidin-2-one

: 439217-28-4
2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / n-BuLi / tetrahydrofuran; hexane / 0.58 h

2: AD mix α; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 22.5 h / 0 - 5 °C

3: 42 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

4: 99 percent / lithium borohydride / methanol; tetrahydrofuran / 4 h / 0 °C

5: 66 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

6: sodium hydride / dimethylformamide / -50 - -10 °C

7: 340 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h

8: 95 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

With 2,6-dimethylpyridine; dmap; AD-mix-α; lithium borohydride; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ol026034o