(4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 265666-17-9
• Molecular Formula: C₃₄H₆₇NO₇Si₂
• Molecular Weight: 658.079
• Mol file: 265666-17-9.mol

Synonyms:(4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (265666-17-9)

Guidance literature:

Multi-step reaction with 3 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

With 2,6-dimethylpyridine; sodium hydrogencarbonate; ozone; In dichloromethane; 3.1: Wittig reaction;

DOI:10.1039/b308305e

Reference yield:

(4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (265666-17-9) → (2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole (265666-22-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

2.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

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

4.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

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

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

6.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

7.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

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

8.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

9.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

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

10.2: 76 percent / N-tosylimidazole / tetrahydrofuran / 3 h / 0 - 20 °C

With hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; 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; 2.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

Reference yield:

(4S,1'R,3'R)-4-[6'-ethoxycarbonyl-1'-(triethylsilanyloxy)-3'-(triisopropylsilanyloxy)-hex-(5'E)-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (265666-17-9) → (2'R,4'R,6'R)-3''-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl}-propane-1'',2''-diol (265666-21-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

2.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

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

4.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

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

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

6.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

7.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

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

8.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

9.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

With hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; 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; 2.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

(2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetaldehyde

(2'R,4'R,6'R)-4-(6'-allyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl)-2-(4-methoxybenzyloxymethyl)-oxazole

(2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole

(2'R,4'R,6'R)-3''-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl}-propane-1'',2''-diol