(3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

Base Information

Chemical Name:(3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile
CAS No.:224579-95-7
Molecular Formula:C₂₃H₃₉NO₄Si
Molecular Weight:421.652
Hs Code.:

Synonyms:(3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

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Chemical Property of (3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

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Technology Process of (3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

There total 10 articles about (3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile 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: 91.0%

: 151-50-8
potassium cyanide

: 224580-05-6
tert-Butyl-[(2S,3R)-3-(4-methoxy-benzyloxy)-2,3-dimethyl-4-(S)-oxiranyl-butoxy]-dimethyl-silane

: 224579-95-7
(3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

Guidance literature:: With lithium perchlorate; In acetonitrile; at 70 ℃; for 12h;
DOI:10.1016/S0040-4039(99)00207-5

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 224579-95-7
(3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / CSA / CH₂Cl₂

2: 86 percent / DIBAL / CH₂Cl₂

3: 97 percent / 2,6-lutidine

4: 1.) O₃, pyr., 2.) Me₂S / 12 h

5: NaBH₄ / ethanol

6: Bu₃P

7: H₂O₂ / tetrahydrofuran

8: K₂OsO₄*H₂O, DHQ₂-PYR / 24 h

9: 86 percent / NaH, tosylimidazole / tetrahydrofuran

10: 91 percent / LiClO₄ / acetonitrile / 12 h / 70 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; potassium osmate(VI); (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); dimethylsulfide; tributylphosphine; camphor-10-sulfonic acid; dihydrogen peroxide; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; ozone; N-tosylimidazole; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(99)00207-5

Reference yield:

: 224580-02-3
(4R,5S)-2-(4-Methoxy-phenyl)-4,5-dimethyl-4-(4-methyl-pent-3-enyl)-[1,3]dioxane

: 224579-95-7
(3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / DIBAL / CH₂Cl₂

2: 97 percent / 2,6-lutidine

3: 1.) O₃, pyr., 2.) Me₂S / 12 h

4: NaBH₄ / ethanol

5: Bu₃P

6: H₂O₂ / tetrahydrofuran

7: K₂OsO₄*H₂O, DHQ₂-PYR / 24 h

8: 86 percent / NaH, tosylimidazole / tetrahydrofuran

9: 91 percent / LiClO₄ / acetonitrile / 12 h / 70 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; potassium osmate(VI); (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); dimethylsulfide; tributylphosphine; dihydrogen peroxide; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; ozone; N-tosylimidazole; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(99)00207-5