219586-42-2

Upstream product

• 72155-45-4 Boc-L-phenylalaninal 
• 79265-30-8 2-(trimethylsilyl)thiazole 

Downstream Products

• 158744-42-4 Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester 
• 219586-44-4 2-<(4S,5S)-4-benzyl-3-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole 
• 219586-43-3 2-<(4S,5R)-4-benzyl-3-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole 
• 134458-64-3 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-formyl-1,3-oxazolidine 
• 174510-86-2 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-formyl-1,3-oxazolidine 
• 187818-11-7 (4S,5R)-5-((R)-1-Amino-2-phenyl-ethyl)-4-benzyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 187818-10-6 (2R,3S,4S)-2-N-benzylhydroxylamine-4-tert-butoxycarbonylamino-1,5-diphenyl-4N,3O-isopropylidene-3-pentanol 
• 187818-12-8 (Z)-N-<(4S,5S)-4-benzyl-3-tert-butoxycarbonyl-2,2-dimethyl-5-methylenyl-1,3-oxazolidinyl>benzylamine N-oxide 
• 187818-05-9 (Z)-N-<(4S,5R)-4-benzyl-3-tert-butoxycarbonyl-2,2-dimethyl-5-methylenyl-1,3-oxazolidinyl>benzylamine N-oxide 
• 124127-29-3 (S)-4-Benzyl-5-thiazol-2-yl-oxazolidin-2-one 
• 136522-18-4 2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 137431-06-2 2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 152683-74-4 3(S)-(tert-Butoxyformamido)-2(S)-hydroxy-4-phenyl-1-butanal 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide 

Relevant academic research and scientific papers

A new method for the solid phase synthesis of hydroxyethylamine peptide bond isosteres: Synthesis of an HIV-1 protease inhibitor and of a β-casomorphin-5 analogue

A solid phase synthesis procedure for the preparation of hydroxyethylamine peptide isosteres is described. Reductive amination of the resin-bound peptide with an α-hydroxyaldehyde, prepared via 2-(trimethylsilyl)thiazole addition to Boc-phenylalaninal or Boc-prolinal, produces the peptides in good yield.

THIAZOLIDINE DERIVATIVES

An object of the present invention is to provide novel thiazolidine derivatives which are useful as drugs. The thiazolidine derivatives according to the present invention are compounds represented by the following general formula [I] and salts thereof, wherein R 1is alkyl, hydroxy, alkoxy, alkoxyalkyl, phenyl, phenylalkyl, phenylalkoxy, phenoxy, phenoxyalkyl, amino, alkylamino or a nonaromatic heterocycle; R 2is H or alkyl; R 3is H, alkyl or phenyl; R 4is H or alkyl; R 5is alkyl, halogenoalkyl, hydroxy, alkoxy, phenyl, phenylalkoxy, phenoxy, carboxyl, alkoxycarbonyl, phenylalkoxycarbonyl or an aromatic heterocycle; A 1is alkylene; and A 2is alkylene.

NOVEL THIAZINE OR PYRAZINE DERIVATIVES

An object of the present invention is to synthesize novel compounds having 3-oxo-3, 4-dihydro-2H-1, 4-thiazine or 2-oxo-1, 2, 3, 4-tetrahydropyrazine as a main skeleton. The present invention relates to compounds represented by the following general formula [I] and salts thereof. In the formula, X is S or R6-(A2)n-N, R1 and R2 are H, alkyl, cycloalkyl or aryl, R3 and R4 are H, alkyl, cycloalkyl, aryl or aromatic heterocycles, R5 is H, alkyl, cycloalkyl, aryl or -A3-A4-R7, R6 is H, alkyl, cycloalkyl, OH, alkoxy, aryl, aryloxy or an aromatic heterocycle, R7 is H, alkyl, OH, alkoxy, aryl, aryloxy, amino, alkylamino, arylamino, an aromatic heterocycle or a nonaromatic heterocycle, A1 is alkylene, A2 is carbonyl or sulfonyl, A3 is alkylene, and A4 is carbonyl or oxalyl.

Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959

Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials.Six approaches for the large-scale synthesis of this compound have been studied.All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5.They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation.The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1.Kilogram quantities of Ro 31-8959 have been prepared using this route.

Stereochemistry Associated with the Addition of 2-(Trimethylsilyl)thiazole to Differentially Protected α-Amino Aldehydes. Applications toward the Synthesis of Amino Sugars ans Sphingosines

The stereochemistry and synthetic utility of the addition of 2-(trimethylsilyl)thiazole (2-TST, 1) to various N-protected α-amino aldehydes is described.The reactions of 1 with N-Boc-L-serinal acetonide (2) and N-Boc-L-threoninal acetonide (3) are essential anti diastereoselective (ds = 85-90percent) in agreement with the Felkin-Anh model for asymmetric induction, whereas the reactions with O-benzyl-NH-Boc-L-serinal (4) and NH-Boc-L-phenylalaninal (5) are syn diastereoselective (ds = 80percent).The reversal of diastereoselectivity is interpreted on the basis of a proton-bridged cyclic Cram model for asymmetric induction.Te anti-adduct derived the N-Boc-L-serinal acetonide (2) was subjected to thiazol-to-formyl unmasking to give a one-carbon higher homologue (i. e., the O,N-protected β-amino-α-hydroxy aldehyde 6a).This material serves as a precursor to ribo- and arabino-4-amino-4-deoxypentoses via a further one-carbon-chain elongation with 2-TST and to a C20 sphingosine via Wittig olefination.The above ribo-amino sugar was transformed via sequential Wittig olefination and reduction into a C18 phytosphingosine.