(4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one

Base Information

• Chemical Name: (4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one
• CAS No.: 911423-94-4
• Molecular Formula: C₃₂H₅₅NO₇Si₂
• Molecular Weight: 621.962
• Mol file: 911423-94-4.mol

Synonyms:(4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one

Chemical Property of (4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one

There total 9 articles about (4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one 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: 95.0%

(4S,5R)-3-[(S)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}-2-hydroxypropanoyl]-4-methyl-5-phenyloxazolidin-2-one (911423-81-9) + t-butyldimethylsiyl triflate (69739-34-0) → (4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one (911423-94-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1002/ejoc.200600113

Reference yield:

3-[(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-propionaldehyde → (4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one (911423-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / NaH₂PO₄; NaClO₂; 2,3-dimethyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 20 °C

2.1: triethylamine; pivaloyl chloride / diethyl ether / 0.5 h / -78 - -30 °C

2.2: 76 percent / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 53 percent / Davis' oxaziridine / tetrahydrofuran / 0.13 h / -92 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 14 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1002/ejoc.200600113

Reference yield:

3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propan-1-ol (911423-78-4) → (4S,5R)-3-[(S)-2-(tert-butyldimethylsilyloxy)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoyl]-4-methyl-5-phenyloxazolidin-2-one (911423-94-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

2.1: 93 percent / NaH₂PO₄; NaClO₂; 2,3-dimethyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 20 °C

3.1: triethylamine; pivaloyl chloride / diethyl ether / 0.5 h / -78 - -30 °C

3.2: 76 percent / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C

4.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

4.2: 53 percent / Davis' oxaziridine / tetrahydrofuran / 0.13 h / -92 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 14 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene; sodium hexamethyldisilazane; pivaloyl chloride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1002/ejoc.200600113

upstream raw materials:

(4S,5R)-3-[(S)-3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}-2-hydroxypropanoyl]-4-methyl-5-phenyloxazolidin-2-one

t-butyldimethylsiyl triflate

3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propan-1-ol

3-{(4R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-2,2,5-trimethyl-1,3-dioxolan-4-yl}propanoic acid