3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone

Base Information

• Chemical Name: 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone
• CAS No.: 345653-68-1
• Molecular Formula: C₃₈H₄₉NO₅Si
• Molecular Weight: 627.896
• Mol file: 345653-68-1.mol

Synonyms:3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone

Chemical Property of 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone

There total 11 articles about 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone 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: 34.0%

(4R,5S)-3-(1-oxo-2-bromoethyl)-4-methyl-5-phenyl-2-oxazolidinone (147595-55-9) + 9(S)-(tert-Butyldiphenylsilyloxy)-4E-decenal (345653-59-0) → 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'S-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone (345653-67-0) + 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone (345653-68-1)

Guidance literature:

With tristriphenylphosphine cobalt chloride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1021/np000502q

Reference yield:

4-methyl-5-phenyloxazolidin-2-one (77943-39-6) → 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone (345653-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

2.1: 32 percent / Co(PPh₃)4 / tetrahydrofuran / 0.17 h / 0 °C

With n-butyllithium; tristriphenylphosphine cobalt chloride; In tetrahydrofuran; hexane; 2.1: Reformatsky reaction;

DOI:10.1021/np000502q

Reference yield:

(S)-2-(tert-butyldiphenylsilyloxy)-1-propanol (97974-23-7) → 3-(11'(S)-(tert-Butyldiphenylsilyloxy)-3'R-hydroxy-6'E-dodecenoyl)-4R-methyl-5S-phenyl-2-oxazolidinone (345653-68-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 64.42 g / pyridine / CH₂Cl₂ / 24.5 h / 0 - 20 °C

2.1: 93 percent / LiBr / tetrahydrofuran / 47 h / Heating

3.1: 76 percent / Li₂CuCl₄ / tetrahydrofuran; diethyl ether / 17 h / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 1 h / 0 - 20 °C

4.2: 68 percent / Br₂; NaOMe / tetrahydrofuran; methanol / 5 - 20 °C

5.1: 75 percent / toluene / 48 h / Heating

6.1: PhLi / tetrahydrofuran; diethyl ether / 0.33 h / 20 °C

6.2: 54 percent / tetrahydrofuran; diethyl ether / 0.67 h / -40 - -30 °C

7.1: 80 percent / aq. AcOH / tetrahydrofuran / 47 h / Heating

8.1: 32 percent / Co(PPh₃)4 / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; borane-THF; dilithium tetrachlorocuprate; tristriphenylphosphine cobalt chloride; acetic acid; phenyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 6.2: Wittig-Schlosser reaction / 8.1: Reformatsky reaction;

DOI:10.1021/np000502q

upstream raw materials:

(4R,5S)-3-(1-oxo-2-bromoethyl)-4-methyl-5-phenyl-2-oxazolidinone

9(S)-(tert-Butyldiphenylsilyloxy)-4E-decenal

4-methyl-5-phenyloxazolidin-2-one

(S)-2-(tert-butyldiphenylsilyloxy)-1-propanol

Downstream raw materials:

11(S)-(tert-Butyldiphenylsilyloxy)-3R-methoxy-6E-dodecenal

Methyl 11(S)-(tert-butyldiphenylsilyloxy)-3R-methoxy-6E-dodecenoate

Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

Methyl 11(S)-(tert-butyldiphenylsilyloxy)-3R-hydroxy-6E-dodecenoate