(3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Base Information

• Chemical Name: (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• CAS No.: 161871-12-1
• Molecular Formula: C₃₄H₄₄N₂O₈Si
• Molecular Weight: 636.817
• Mol file: 161871-12-1.mol

Synonyms:(3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Chemical Property of (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

There total 7 articles about (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-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: 21.0%

ox-glycyl chloride (61964-71-4) + (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amino}-butyric acid methyl ester (161871-11-0) → (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[2-(2-oxo-4,5-diphenyl-oxazol-3-yl)-acetylamino]-butyric acid methyl ester + (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (161871-12-1) + (3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (161970-86-1)

Guidance literature:

With TEA; In dichloromethane; Yields of byproduct given;

DOI:10.1016/0040-4039(94)02294-L

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (161871-12-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / imidazole / dimethylformamide / 1) 0 deg C, 30 min; 2) 0 deg C --> rt, overnight

2: MgSO₄ / CH₂Cl₂ / 4 h / 0 °C

3: Et₃N / CH₂Cl₂ / 1) -18 deg C, 2 h; 2) -10 --> 0 deg C, 30 min

With 1H-imidazole; magnesium sulfate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo951651u

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (161871-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / CH₂Cl₂ / 4 h / 0 °C

2: Et₃N / CH₂Cl₂ / 1) -18 deg C, 2 h; 2) -10 --> 0 deg C, 30 min

With magnesium sulfate; triethylamine; In dichloromethane;

DOI:10.1021/jo951651u

upstream raw materials:

ox-glycyl chloride

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amino}-butyric acid methyl ester

tert-butyldimethylsilyl chloride

3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one

Downstream raw materials:

(E)-2-[(2S,3S)-2-((S)-1,2-Dihydroxy-ethyl)-4-oxo-3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-azetidin-1-yl]-but-2-enoic acid methyl ester

(E)-2-[(2S,3S)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-oxo-3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-azetidin-1-yl]-but-2-enoic acid methyl ester