734548-35-7

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 178899-79-1 (2S,3R)-2-amino-3-methylbutane-1,4-diol 
• 137172-54-4 3(S)-[(t-butoxycarbonyl)amino]-2(S)-methyl - γ-butyrolactone 
• 138219-39-3 2-bromo-2-(N-tert-butoxycarbonylamino)acetic acid methyl ester 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 
• 178755-12-9 (2S,3R-)-2-[N-Benzyl-N-(9-phenylfluoren-9-yl)]amino-3-methylbutane-1,4-diol 
• 503839-49-4 (2R,3R)-3-tert-butylsulfanylcarbonyl-2-dodecanoylamino-butyric acid ethyl ester 
• 76943-94-7 (Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene 
• 81357-15-5 [(E)-tert-Butoxycarbonylimino]-acetic acid methyl ester 

Relevant academic research and scientific papers

Enantio- and diastereoselective, stereospecific Mannich-type reactions in water

Catalytic asymmetric Mannich-type reactions in water proceeded in high yields and selectivities using a combination of ZnF2 and a chiral diamine that has the methoxy groups on the aromatic rings. In these reactions, either syn- or anti-Mannich

Catalytic, asymmetric Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen

(Matrix presented) Catalytic, enantioselective Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen are described. Several N-carbamate-protected α-imino esters, which are readily prepared from 2-bromoglycine esters using a polymer-supported amine, reacted with silicon enolates to afford the desired adducts in high yields with high enantioselectivity using a copper(II)-diamine complex. Easy deprotection of the product amine and transformation to free o-amino acid derivatives have also been demonstrated.

Catalytic, asymmetric Mannich-type reactions of N-acylimino esters: Reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivatives

In the presence of a catalytic amount of Cu(OTf)2-chiral diamine 3e complex, N-acylimino esters reacted with silyl enol ethers to afford the corresponding Mannich-type adducts in high yields with high enantioselectivities. A wide variety of silyl enol ethers derived from ketones, as well as esters and thioesters, reacted smoothly. In the reactions of α-substituted silyl enol ethers (α-methyl or benzyloxy), the desired syn-adducts were obtained in high yields with high diastereo- and enantioselectivities. Several intermediates for the synthesis of biologically important compounds were prepared using this novel catalytic asymmetric Mannich-type reaction, and at the same time, absolute and relative stereochemical assignments were made. In addition, it has been revealed that alkyl vinyl ethers reacted with N-acylimino esters in the presence of a catalytic amount of the Cu(II) catalyst to give the corresponding Mannich-type adducts in high yields with high enantioselectivities. This is the first example of catalytic asymmetric Mannich-type reactions with alkyl vinyl ethers. The reaction mechanism, structure of chiral catalyst-electrophile complexes, and transition states of these catalytic asymmetric reactions were assumed based on X-ray crystallographic analysis of the Cu(II)-chiral amine complex, PM3 calculations, and FT-IR analyses, etc. Finally, (1R,3R)-N-(3-hydroxy- 1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12, 1), a new inhibitor of ceramide trafficking from endoplasmic reticulum to the site of sphingomyerin (SM) synthesis, has been synthesized efficiently using the present Mannich-type reaction as a key step. The synthesis involved three steps (two-pot), and total yield was 82.9%.

Quinoline carboxylic acid

5-Amino-7-((3S,4S)-3-amino-4-methyl (or ethyl)-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid or a pharmacologically acceptable salt thereof represented by the following formula wherein asymmetric carbon atoms

A large-scale preparation of (3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine and its analogs from L-aspartic acid

(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine (12a) was synthesized from L-aspartic acid (4) on a large scale. Methylation of dimethyl (2S)-N-benzyl-N-(9-phenylfluoren-9-yl)aspartate (5), easily derived from 4, with methyl iodide gave (3R)-3-methylaspartate (6a) in 91% yield with high diastereoselectivity. Reduction of 6a with lithium aluminum hydride, followed by hydrogenolysis, protection with di-tert-butyl dicarbonate, and mesylation gave 10a in 89% overall yield. Subsequently, reaction of 10a with benzylamine under a nitrogen atmosphere at room temperature, followed by hydrogenolysis, gave the target compound (12a) in 65% overall yield. In a similar manner to that described for the preparation of 12a from 5, compound 5 was converted into 4-ethyl and 4-propyl derivatives (12b,c) in 34% and 38% overall yields.

Isoindoline derivatives

Optically active 8-methoxyquinolonecarboxylic acids represented by the formula (I) wherein R1 is lower alkyl have been found to possess potent antibacterial activity against both Gram-negative and Gram-positive bacteria. The compounds may be synthesized from novel optically active intermediates.