Practical Synthesis of Triethylammonium (Z)-2-[2-(Boc-amino)thiazol-4-yl]-2-(trityloxyimino)acetate, the Side Chain of Cefmatilen

2005 ◽  
Vol 9 (1) ◽  
pp. 57-61 ◽  
Author(s):  
Yoshihisa Goto ◽  
Yoshiyuki Masui ◽  
Yoji Kitaura ◽  
Tatsuya Kobayashi ◽  
Hisanori Takahashi ◽  
...  
Keyword(s):  
Side Chain ◽  
Practical Synthesis

scholarly journals Practical synthesis of 4-aryl- and 4-heteroarylazetidin-2-ones: applications in the synthesis of the Taxol® side chain

1994 ◽  
Vol 72 (10) ◽  
pp. 2131-2136 ◽  
Author(s):  
Allan W. Rey ◽  
Robert Droghini ◽  
James L. Douglas ◽  
Purushotham Vemishetti ◽  
Susan D. Boettger ◽  
...  
Keyword(s):  
Side Chain ◽  
Staudinger Reaction ◽  
Protecting Group ◽  
Practical Synthesis

A convenient, high-yielding procedure has been developed for the kilogram-scale synthesis of (±)-cis-3-acetoxy-4-phenylazetidin-2-one (3), a β-lactam that has been used in the semi-synthesis of Taxol®. The Staudinger reaction between hydrobenzamide (5) and acetoxyacetyl chloride in the presence of a base provided the α-benzylideneiminotoluene protected β-lactam 8. Without isolation of the intermediate β-lactam, the protecting group was removed under various reductive or hydrolytic conditions. The overall yields were about 80%. The synthesis of other (±)-cis-4-aryl- and 4-heteroarylazetidin-2-ones by this methodology has also been accomplished. These compounds are of value for the synthesis of 3′-Taxol® side-chain analogs and their preparation demonstrates the generality of this approach.

ChemInform Abstract: Practical Synthesis of Taxol Side Chain.

ChemInform ◽  
2010 ◽  
Vol 29 (46) ◽  
pp. no-no
Author(s):  
H.-J. HA ◽  
G.-S. PARK ◽  
Y.-G. AHN ◽  
G. S. LEE
Keyword(s):  
Side Chain ◽  
Practical Synthesis

A practical synthesis of the lipophilic side chain of the polyoxypeptins

2001 ◽  
Vol 42 (13) ◽  
pp. 2431-2434 ◽  
Author(s):  
Miguel Lorca ◽  
Michio Kurosu
Keyword(s):  
Side Chain ◽  
Practical Synthesis

scholarly journals Practical Synthesis of 1,1′-Binaphthyl-2-carboxylic Acids via Side Chain Oxidation of 2-Methyl-1,1′-binaphthyls

1986 ◽  
Vol 59 (6) ◽  
pp. 2044-2046 ◽  
Author(s):  
Sotaro Miyano ◽  
Shin-ichi Okada ◽  
Toshiyuki Suzuki ◽  
Shigeru Handa ◽  
Harukichi Hashimoto
Keyword(s):  
Carboxylic Acids ◽  
Side Chain ◽  
Chain Oxidation ◽  
Practical Synthesis

ChemInform Abstract: A Practical Synthesis of the Lipophilic Side Chain of the Polyoxypeptins.

ChemInform ◽  
2010 ◽  
Vol 32 (26) ◽  
pp. no-no
Author(s):  
Miguel Lorca ◽  
Michio Kurosu
Keyword(s):  
Side Chain ◽  
Practical Synthesis

ChemInform Abstract: Practical Synthesis of 4-Aryl- and 4-Heteroarylazetidin-2-ones: Applications in the Synthesis of the Taxol Side Chain.

ChemInform ◽  
2010 ◽  
Vol 26 (18) ◽  
pp. no-no ◽  
Author(s):  
A. W. REY ◽  
R. DROGHINI ◽  
J. L. DOUGLAS ◽  
P. VEMISHETTI ◽  
S. D. BOETTGER ◽  
...  
Keyword(s):  
Side Chain ◽  
Practical Synthesis
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