allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate

Base Information

• Chemical Name: allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate
• CAS No.: 113599-69-2
• Molecular Formula: C₃₈H₄₆N₂O₅Si
• Molecular Weight: 638.879
• Mol file: 113599-69-2.mol

Synonyms:allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate

Chemical Property of allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate

There total 7 articles about allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate 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%

cyclopropanecarboxylic acid chloride (4023-34-1) + allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-(tritylamino)-1-azetidinyl>acetate (113599-63-6) → allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate (113599-69-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jm00401a020

Reference yield:

allyl bromoacetate (40630-84-0) → allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate (113599-69-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent

2: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

With lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1039/c39870001283

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate (113599-69-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Et₃N, 4-(dimethylamino)pyridine, 2.) KF / 1.) DMF, 1 h, 2.) HOAc, 1 h

2: H₂ / 10percent Pd on charcoal / ethyl acetate / 3 h

3: NEt₃ / CH₂Cl₂ / 1.5 h

4: 59 percent / tetrabutylammonium bromide, KOH / tetrahydrofuran / 20 h

5: 95 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C

With dmap; potassium fluoride; potassium hydroxide; tetrabutylammomium bromide; hydrogen; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm00401a020

upstream raw materials:

cyclopropanecarboxylic acid chloride

allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-(tritylamino)-1-azetidinyl>acetate

allyl bromoacetate

(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone

Downstream raw materials:

(6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

allyl (6S,7S)-3-cyclopropyl-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

allyl 2-<(3S,4S)-4-(hydroxymethyl)-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-3-cyclopropylpropanoate