Substance Overview for Hydroxyacetic acid butyl ester

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.


1993 ◽  
Vol 34 (46) ◽  
pp. 7409-7412 ◽  
Author(s):  
Pierre Chevallet ◽  
Patrick Garrouste ◽  
Barbara Malawska ◽  
Jean Martinez

2014 ◽  
Vol 229 (2) ◽  
pp. 127-128 ◽  
Author(s):  
Chuanhong Zhang ◽  
Jianguo Lin ◽  
Gaochao Lv ◽  
Yang Cao ◽  
Shineng Luo

Abstract C22H23N3O4, triclinic, P1¯ (no. 2), a = 6.992(3) Å, b = 8.159(4) Å, c = 18.778(8) Å, α = 92.118(7)°, β = 93.463(7)°, γ = 101.623(7)°, V = 1045.9 Å3, Z = 2, Rgt(F) = 0.0576, wRref(F2) = 0.1778, T = 296 K.


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