(2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate

Base Information

• Chemical Name: (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate
• CAS No.: 1450899-61-2
• Molecular Formula: C₂₅H₄₂O₅Si
• Molecular Weight: 450.691
• Mol file: 1450899-61-2.mol

Synonyms:(2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate

Chemical Property of (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate

There total 10 articles about (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate 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: 96.0%

(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoic acid (1450899-59-8) + allyl bromide (106-95-6) → (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate (1450899-61-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jo401248n

Reference yield:

3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde (96013-95-5) → (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate (1450899-61-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrahydrofuran / 1.08 h / -10 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

3.1: titanium tetrachloride; titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.58 h / Inert atmosphere

3.2: 0.58 h / -5 °C / Inert atmosphere

4.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane; toluene / 5 h / -5 - 0 °C / Inert atmosphere

5.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 18.08 h / 0 - 20 °C / Inert atmosphere

6.1: sodium tetrahydroborate / tetrahydrofuran; water / 14 h / 20 °C

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

8.1: D-Prolin / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere

9.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 1 h / 0 °C

10.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 2,6-di-tert-butyl-pyridine; 2-methyl-but-2-ene; dimethylsulfide borane complex; titanium tetrachloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; D-Prolin; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo401248n

Reference yield:

1-(3-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol → (2R,3R,4S,7S)-allyl-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoate (1450899-61-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

2.1: titanium tetrachloride; titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.58 h / Inert atmosphere

2.2: 0.58 h / -5 °C / Inert atmosphere

3.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane; toluene / 5 h / -5 - 0 °C / Inert atmosphere

4.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 18.08 h / 0 - 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / tetrahydrofuran; water / 14 h / 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3.08 h / 0 - 20 °C / Inert atmosphere

7.1: D-Prolin / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere

8.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 1 h / 0 °C

9.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 2,6-di-tert-butyl-pyridine; 2-methyl-but-2-ene; dimethylsulfide borane complex; titanium tetrachloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; D-Prolin; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo401248n

upstream raw materials:

(2R,3R,4S,7S)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-3-hydroxy-7-methoxy-2,4-dimethylheptanoic acid

allyl bromide

C₁₉H₃₄O₃Si

3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde

Downstream raw materials:

(2R,3R,4S,7S)-allyl-3-((3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pentanoyloxy)-7-(3-(tert-butyldimethylsilyloxy)phenyl)-7-methoxy-2,4-dimethylheptanoate