145280-11-1

Basic information

• Product Name: Glycine, N-[(1,1-dimethylethoxy)carbonyl]-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• CAS NO: 145280-11-1
• Molecular Formula: C17H31NO4
• Molecular Weight: 313.437
• Mol File: 145280-11-1.mol

Chemical Properties

• CAS DataBase Reference: Glycine, N-[(1,1-dimethylethoxy)carbonyl]-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, N-[(1,1-dimethylethoxy)carbonyl]-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(145280-11-1)
• EPA Substance Registry System: Glycine, N-[(1,1-dimethylethoxy)carbonyl]-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(145280-11-1)

Safety Data

• Hazardous Substances Data: 145280-11-1(Hazardous Substances Data)

Upstream product

• 7377-98-2 (-)-menthyl chloroacetate 
• 2216-51-5 (-)-menthol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 63254-60-4 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-aminoacetate 
• 4530-20-5 BOC-glycine 

Downstream Products

• 145280-13-3 (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)imino>acetate 
• 1268444-43-4 (-)-menthyl N-(1,3-dithiolan-2-ylidene)glycinate 
• 1268444-61-6 (-)-menthyl N-(1,3-dithiolan-2-ylidene)-α-(2-chloro-4-nitrophenyl)glycinate 
• 154108-97-1 (S)-3-Acetyl-2-tert-butoxycarbonylamino-4-[(E)-hydroxyimino]-pentanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 154108-95-9 (1R,3R,4S)-menthyl (2S)-N-t-BOC-3-acetyl-4-oxonorvaline 
• 154108-96-0 (1R,3R,4S)-menthyl (2S)-N-t-BOC-2-(3,5-dimethyl-4-pyrazolyl)glycinate 
• 395074-09-6 1-(1R,2S,5R)-menthyl 3-ethyl (1R)-1-benzyloxycarbonylamino-3-cyclopentenedicarboxylate 
• 395074-10-9 1-(1R,2S,5R)-menthyl 3-ethyl (1S)-1-benzyloxycarbonylamino-3-cyclopentenedicarboxylate 
• 395074-01-8 (1R,2S,5R)-menthyl-2-(diphenylmethylideneamino)propenoate 
• 130156-98-8 (1R,2S,5R)-menthyl-N-(diphenylmethylidene)-glycinate 
• 886116-90-1 (2R,3S,4S,5R)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 886116-88-7 (2S,3R,4R,5S)-5-(4-Cyano-phenyl)-3-fluoro-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 886116-89-8 (2R,3S,4S,5R)-3-Fluoro-5-phenyl-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 886116-87-6 (2S,3R,4R,5S)-3-Fluoro-5-phenyl-pyrrolidine-2,4-dicarboxylic acid 4-ethyl ester 2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 

Relevant articles and documents

Synthesis of nitroaryl derivatives of glycine via oxidative nucleophilic substitution of hydrogen in nitroarenes

Carbanion of ethyl N-(1,3-dithiolan-2-ylidene)glycinate adds to activated nitroarenes mostly in para position to the nitro group. Subsequent oxidation of the resulting σH adducts with DDQ gave respective α-nitroarylated glycine derivatives in moderate yields. The reaction of esters of chiral alcohols such as (-)-menthol or (-)-8-phenylmenthol proceeds with a moderate or high diastereoselectivity leading to enantiomerically enriched nitroarylglycines. ARKAT-USA, Inc.

First 1,3-dipolar cycloaddition of azomethine ylides with (E)-ethyl 3-fluoroacrylate: Regio- and stereoselective synthesis of enantiopure fluorinated prolines

Enantiopure fluorinated prolines with four chiral centers were obtained from 1,3-dipolar cycloaddition of azomethine ylides and (E)-ethyl 3-fluoroacrylate. Georg Thieme Verlag Stuttgart.

Synthesis and biological evaluation of menthol-based derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)

Compound 1 was identified by high throughput screening as a novel PAI-1 inhibitor. Optimization of the B and C-segments of 1 resulted in a series of structurally simplified compounds with improved potency. The synthesis and SAR data of these compounds are presented here.

Synthesis and biological activities of conformationally restricted cyclopentenyl-glutamate analogues

An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 μM) and mGlu2 (EC50 45 μM) receptors.

A radical-organometallic glycine synthon. Preparation of homochiral heterocyclic α-amino acids

Co(Acac)2 reacts with (1) and (d)-menthyl N-BOC-2-bromoglycinates to give (1)- and (d)-menthyl N-BOC-3-acetylnorvalinates, which are converted into homochiral 2-(3,5-dimethyl-4-pyrazolyl)glycine and 2-(3,5-dimethyl)-4-isoxazolylglycine.

The asymmetric synthesis of α-amino acids via the addition of grignard reagents to imine derivatives

The ester-8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S-N-Boc-2-alkylgrycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid.