55674-63-0

Usage

Chemical Properties

Colorless liquid viscid liquid

InChI:InChI=1/C11H21NO4/c1-5-6-7-8(9(13)14)12-10(15)16-11(2,3)4/h8H,5-7H2,1-4H3,(H,12,15)(H,13,14)/t8-/m1/s1

Upstream product

• 327-56-0 D-norleucine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 116611-53-1 [(S)-2-Benzenesulfonyl-1-(tetrahydro-pyran-2-yloxymethyl)-pentyl]-carbamic acid tert-butyl ester 
• 116611-50-8 ((S)-2-Benzenesulfonyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester 
• 116611-47-3 Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-3-(tetrahydro-pyran-2-yloxy)-propyl ester 
• 116611-48-4 [(S)-2-Phenylsulfanyl-1-(tetrahydro-pyran-2-yloxymethyl)-ethyl]-carbamic acid tert-butyl ester 
• 116611-63-3 methyl N-(tert-butoxycarbonyl)-O-(tetrahydro-2H-pyran-2-yl)-L-serinate 
• 116611-46-2 tert-butyl [(2R)-1-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl]carbamate 
• 116696-85-6 (2S)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 116611-49-5 ((S)-1-Hydroxymethyl-2-phenylsulfanyl-ethyl)-carbamic acid tert-butyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 188347-85-5 (4R, 5S)-4-butyl-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-2-oxazolidinone 
• 116640-17-6 tert-butyl (R)-(1-hydroxyhexan-2-yl)carbamate 

Downstream Products

• 116611-59-7 D-N-Boc-nor-leucine methyl ester 
• 169448-61-7 (R)-N-benzyl 2-(N'-t-butoxycarbonylamino)hexanamide 
• 1312306-55-0 (R)-N-benzyl 2-aminohexanamide 
• 120059-68-9 H-D-Nle-Trp-Nle-Asp(OBzl)-Phe-NH₂*TFA 
• 173326-37-9 N-cis-2,6-dimethylpiperidinocarbonyl-γ-methylleucyl-D-1-(methoxycarbonyl)tryptophanyl-D-norleucine 
• 173204-47-2 HCl*D-Nle-OBzl 
• 169448-55-9 2(R)-tert-butoxycarbonylaminohexanal 

Relevant academic research and scientific papers

Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities

Pharmacological management remains the primary method to treat epilepsy and neuropathic pain. We have advanced a novel class of anticonvulsants termed functionalized amino acids (FAAs). In this study, we examine FAA derivatives from which the terminal acetyl moiety was removed and termed these compounds primary amino acid derivatives (PAADs). Twenty-seven PAADs were prepared; the central C(2) R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the d-amino acid configuration ((R)-stereoisomer). These values surpassed the activities of several clinical antiepileptic drugs. The C(2) (R)-ethyl and C(2) (R)-isopropyl PAADs also displayed excellent activities in the mouse (ip) formalin neuropathic pain model. Significantly, unlike the FAA structure-activity relationship, PAAD anticonvulsant activity increased upon substitution of a methylene unit for a heteroatom in the R-substituent that was one atom removed from the C(2) site, suggesting that these PAADs function by a different pathway than FAAs.

Chiral electrophilic 'glycinal' equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

The thermal reaction of 3-[(1S)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as α-aminoaldehyde templates useful for the synthesis of a wide variety of optically active α-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones.

A NOVEL APPROACH TO THE SYNTHESIS OF OPTICALLY PURE NON PROTEIN α-AMINO ACIDS IN BOTH L AND D CONFIGURATIONS FROM L-SERINE

Efficient syntheses of (2R)-2-Boc-amino-3-phenylsulfonyl-1-propanol 3 and its enantiomer 9 from L-serine are described.The potential of these compounds in a novel general method for the synthesis of optically pure non protein α-amino acids in both the L and D configurations is exemplified by the preparation of N-Boc-L-and D-homophenylalanine,-norvaline and -norleucine.

Novel decapeptide amide analogs of leuteinizing hormone-releasing hormone

The novel decapeptide amide derivatives of the formula wherein R1 is Tyr or Phe; R2 is D-Nle, D-Nva, D-Abu, D-Phe, D-Ser, D-Thr or D-Met and R3 is Leu, Ile or Nle have a strong ovulation inducing activity.