(4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:265666-14-6
Molecular Formula:C₂₈H₅₃NO₇Si
Molecular Weight:543.817
Hs Code.:

(4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Synonyms:(4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 265666-14-6
(4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

2.1: ozone; NaHCO₃ / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 95 percent / PPh₃ / CH₂Cl₂ / 14 h / 20 °C

3.1: 87 percent / CH₂Cl₂ / 14 h / 20 °C

4.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

5.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

With 2,6-dimethylpyridine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; ozone; In tetrahydrofuran; dichloromethane; 3.1: Wittig reaction / 5.1: oxy-anion intramolecular Michael reaction;
DOI:10.1039/b308305e

Reference yield:

: 265666-14-6
(4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 265666-25-9
(2'S,4'R,6'R,5R)-methanesulfonic acid 5,7-dihydroxy-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-3-methyleneheptyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: aq. HCl / dioxane / 1.33 h / 20 °C

2.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4.1: PPh₃; 2,6-di-tert-butylpyridine; dibromotetrachloroethane / CH₂Cl₂ / 3 h / 20 °C

4.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

5.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

6.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

6.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

7.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

8.1: NaH / tetrahydrofuran / 1 h / 20 °C

8.2: 76 percent / N-tosylimidazole / tetrahydrofuran / 3 h / 0 - 20 °C

9.1: t-BuLi / pentane; tetrahydrofuran / 0.5 h / -78 °C

9.2: lithium 2-thienylcyanocuprate / pentane; tetrahydrofuran / 1 h / -40 °C

9.3: 20 percent / pentane; tetrahydrofuran / 24 h / -78 - 0 °C

10.1: Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

11.1: 25 mg / 10-camphorsulfonic acid / methanol / 1.5 h / 20 °C

With hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; (1S)-10-camphorsulfonic acid; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; toluene; tert-butyl alcohol; pentane;
DOI:10.1039/b308305e

Reference yield:

: 265666-14-6
(4S,2'R,4'R,6'S)-4-[6'-ethoxycarbonylmethyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 657389-92-9
Methanesulfonic acid 3-((R)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-1-{(2S,4R,6R)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: aq. HCl / dioxane / 1.33 h / 20 °C

2.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4.1: PPh₃; 2,6-di-tert-butylpyridine; dibromotetrachloroethane / CH₂Cl₂ / 3 h / 20 °C

4.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

5.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

6.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

6.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

7.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

8.1: NaH / tetrahydrofuran / 1 h / 20 °C

8.2: 76 percent / N-tosylimidazole / tetrahydrofuran / 3 h / 0 - 20 °C

9.1: t-BuLi / pentane; tetrahydrofuran / 0.5 h / -78 °C

9.2: lithium 2-thienylcyanocuprate / pentane; tetrahydrofuran / 1 h / -40 °C

9.3: 20 percent / pentane; tetrahydrofuran / 24 h / -78 - 0 °C

10.1: Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

With hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene; tert-butyl alcohol; pentane;
DOI:10.1039/b308305e