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

Base Information

Chemical Name:(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-benzoyloxy-1-methyl)-2-butenyl>-1-azetidin-2-one
CAS No.:224780-72-7
Molecular Formula:C₃₀H₄₅NO₈Si
Molecular Weight:575.775
Hs Code.:

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

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

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

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

There total 6 articles about (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-benzoyloxy-1-methyl)-2-butenyl>-1-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: 92.0%

: 541-41-3
chloroformic acid ethyl ester

: 224780-70-5
(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-benzoyloxy-1-methyl)-2-butenyl>-1-<(ethoxycarbonyl)methyl>azetidin-2-one

: 224780-72-7
(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-benzoyloxy-1-methyl)-2-butenyl>-1-azetidin-2-one

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1002/(SICI)1099-0690(199903)1999:3<621::AID-EJOC621>3.0.CO;2-A

Reference yield:

: 105320-15-8
(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(1-hydroxymethyl-vinyl)-azetidin-2-one

: 224780-72-7
(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-benzoyloxy-1-methyl)-2-butenyl>-1-azetidin-2-one

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: 88 percent / Et₃N / CH₂Cl₂ / 16 h / 0 °C

6: 93 percent / LiHMDS / tetrahydrofuran / 2 h / -40 °C

7: 92 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

With oxalyl dichloride; [(R)-BINAP]RuBr₂; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/(SICI)1099-0690(199903)1999:3<621::AID-EJOC621>3.0.CO;2-A

Reference yield:

: 111187-44-1
3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-hydroxy-2-methylethyl)>azetidin-2-one

: 224780-72-7
(3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S,2E)-(4-benzoyloxy-1-methyl)-2-butenyl>-1-azetidin-2-one

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: 88 percent / Et₃N / CH₂Cl₂ / 16 h / 0 °C

5: 93 percent / LiHMDS / tetrahydrofuran / 2 h / -40 °C

6: 92 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1002/(SICI)1099-0690(199903)1999:3<621::AID-EJOC621>3.0.CO;2-A