(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one
• CAS No.: 224780-82-9
• Molecular Formula: C₂₉H₄₅NO₉SSi
• Molecular Weight: 611.829

Synonyms:(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one

Chemical Property of (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one

There total 5 articles about (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)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:

(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(1-hydroxymethyl-vinyl)-azetidin-2-one (105320-15-8) → (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one (224780-82-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / H₂, (+)-(R)-BinapRuBr₂ / methanol / 60 h / 25 °C / 12751 Torr

2: 84 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -60 °C

3: 99 percent / tetrahydrofuran / 2 h / 60 °C

4: 90 percent / DIBALH / tetrahydrofuran; CH₂Cl₂ / 1.) -78 deg C, 2 h; 2.) 0.5 h, 25 deg C

5: 96 percent / CH₂Cl₂; pyridine / 2 h / 25 °C

6: 83 percent / LiHMDS / tetrahydrofuran / 2 h / -40 °C

7: 1.) LiHMDS; 2.) Oxone, wet Al₂O₃ / 1.) THF, -78 deg C, 3 h; 2.) chloroform, reflux, 4 h

With aluminum oxide; Oxone; oxalyl dichloride; [(R)-BINAP]RuBr₂; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199903)1999:3<621::AID-EJOC621>3.0.CO;2-A

Reference yield:

3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-hydroxy-2-methylethyl)>azetidin-2-one (111187-44-1) → (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one (224780-82-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -60 °C

2: 99 percent / tetrahydrofuran / 2 h / 60 °C

3: 90 percent / DIBALH / tetrahydrofuran; CH₂Cl₂ / 1.) -78 deg C, 2 h; 2.) 0.5 h, 25 deg C

4: 96 percent / CH₂Cl₂; pyridine / 2 h / 25 °C

5: 83 percent / LiHMDS / tetrahydrofuran / 2 h / -40 °C

6: 1.) LiHMDS; 2.) Oxone, wet Al₂O₃ / 1.) THF, -78 deg C, 3 h; 2.) chloroform, reflux, 4 h

With aluminum oxide; Oxone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199903)1999:3<621::AID-EJOC621>3.0.CO;2-A

Reference yield:

(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S)-1-(formyl)ethyl>azetidin-2-one (159496-98-7) → (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-(<(phenylsulfonyl)ethoxycarbonyl>methyl)azetidin-2-one (224780-82-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / tetrahydrofuran / 2 h / 60 °C

2: 90 percent / DIBALH / tetrahydrofuran; CH₂Cl₂ / 1.) -78 deg C, 2 h; 2.) 0.5 h, 25 deg C

3: 96 percent / CH₂Cl₂; pyridine / 2 h / 25 °C

4: 83 percent / LiHMDS / tetrahydrofuran / 2 h / -40 °C

5: 1.) LiHMDS; 2.) Oxone, wet Al₂O₃ / 1.) THF, -78 deg C, 3 h; 2.) chloroform, reflux, 4 h

With aluminum oxide; Oxone; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199903)1999:3<621::AID-EJOC621>3.0.CO;2-A

upstream raw materials:

diphenyldisulfane

(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-ethoxycarbonyloxy-1-methyl)-2-butenyl>-1-<(ethoxycarbonyl)methyl>azetidin-2-one

(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(1-hydroxymethyl-vinyl)-azetidin-2-one

3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-hydroxy-2-methylethyl)>azetidin-2-one

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