exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

Base Information

Chemical Name:exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one
CAS No.:461412-42-0
Molecular Formula:C₂₇H₃₆N₂O₄Si
Molecular Weight:480.679
Hs Code.:

Synonyms:exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

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Chemical Property of exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

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Technology Process of exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

There total 4 articles about exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-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: 39.0%

: 34713-98-9
(R)-(-)-α-methoxyphenylacetyl chloride

: exo-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

: 461412-42-0
exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

: 461412-43-1
exo-(5R,6S)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

Guidance literature:: exo-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.25h;

(R)-(-)-α-methoxyphenylacetyl chloride; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;
DOI:10.1002/1521-3765(20020603)8:11<2464::AID-CHEM2464>3.0.CO;2-S

Reference yield:

: 461412-31-7
N-acetyl-N'-(3-oxo-3-phenylpropyl)imidazolidin-2-one

: 461412-42-0
exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 40 percent / toluene / 3 h / 35 °C / Irradiation

2.1: 2,6-lutidine / CH₂Cl₂ / 18 h / 0 - 20 °C

3.1: 363 mg / K₂CO₃ / methanol / 3 h / 20 °C

4.1: LHMDS / tetrahydrofuran / 0.25 h / -78 °C

4.2: 39 percent / tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Norrish-Yang cyclization;
DOI:10.1002/1521-3765(20020603)8:11<2464::AID-CHEM2464>3.0.CO;2-S

Reference yield:

: exo-3-acetyl-6-hydroxy-6-phenyl-1,3-diazabicyclo[3.3.0]octan-2-one

: 461412-42-0
exo-(5S,6R)-3-((R)-methoxyphenylacetyl)-6-phenyl-6-[(triethylsilyl)oxy]-1,3-diazabicyclo[3.3.0]octan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 18 h / 0 - 20 °C

2.1: 363 mg / K₂CO₃ / methanol / 3 h / 20 °C

3.1: LHMDS / tetrahydrofuran / 0.25 h / -78 °C

3.2: 39 percent / tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/1521-3765(20020603)8:11<2464::AID-CHEM2464>3.0.CO;2-S