(1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

Base Information

• Chemical Name: (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate
• CAS No.: 403666-62-6
• Molecular Formula: C₂₆H₄₀O₅Si
• Molecular Weight: 460.686

Synonyms:(1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

Chemical Property of (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

There total 9 articles about (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate 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: 85.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1'S,1R,2R,3R,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate (403666-32-0) → (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate (403666-62-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.0.CO;2-J

Reference yield:

pivaloyl chloride (3282-30-2) → (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate (403666-62-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / DMAP; NEt₃ / CH₂Cl₂ / 1.67 h / 0 - 20 °C

2.1: 85 percent / DBU / acetonitrile / 1.67 h / 16 - 18 °C / Irradiation

3.1: aq. CeCl₃*5H₂O / tetrahydrofuran / 10 h / 0 °C

3.2: 99 percent / aq. NaBH₄ / tetrahydrofuran / 3 h / 0 - 11 °C

4.1: DMAP; pyridine / CH₂Cl₂ / 3 h / 0 - 40 °C

5.1: 311 mg / nBu₄NNO₂ / dimethylsulfoxide / 16 h / 20 °C

6.1: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C

With pyridine; 1H-imidazole; dmap; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tetrabutylammonium nitrite; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.0.CO;2-J

Reference yield:

(-)-(1'S,2S)-2α-(1-Phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one (209852-87-9) → (1'S,1R,2S,3R,4R,5S)-(2-(1'-phenylethoxy)-3-(tert-butyldimethylsilanyloxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate (403666-62-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / LDA; NEt₃ / tetrahydrofuran; hexane / -78 °C

2.1: aq. mCPBA / tetrahydrofuran / 2.5 h / 0 - 20 °C

2.2: 78 percent / TFA / tetrahydrofuran; H₂O / 4 h / 20 °C

3.1: 95 percent / DMAP; NEt₃ / CH₂Cl₂ / 1.67 h / 0 - 20 °C

4.1: 85 percent / DBU / acetonitrile / 1.67 h / 16 - 18 °C / Irradiation

5.1: aq. CeCl₃*5H₂O / tetrahydrofuran / 10 h / 0 °C

5.2: 99 percent / aq. NaBH₄ / tetrahydrofuran / 3 h / 0 - 11 °C

6.1: DMAP; pyridine / CH₂Cl₂ / 3 h / 0 - 40 °C

7.1: 311 mg / nBu₄NNO₂ / dimethylsulfoxide / 16 h / 20 °C

8.1: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C

With pyridine; 1H-imidazole; dmap; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetrabutylammonium nitrite; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.0.CO;2-J

upstream raw materials:

tert-butyldimethylsilyl chloride

(1'S,1R,2R,3R,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

pivaloyl chloride

(-)-(1'S,2S)-2α-(1-Phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one

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