117997-58-7

Basic information

• Product Name: tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate
• Synonyms: tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate
• CAS NO: 117997-58-7
• Molecular Weight: 325.448
• Mol File: 117997-58-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate(117997-58-7)
• EPA Substance Registry System: tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate(117997-58-7)

Safety Data

• Hazardous Substances Data: 117997-58-7(Hazardous Substances Data)

Upstream product

• 121533-55-9 (4S,5S)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-5-vinyloxazolidine 
• 104856-05-5 (3RS,4S)-4-<(tert-butyloxy)carbonyl>-5-(cyclohexylmethyl)-3-hydroxy-1-pentene 
• 138448-18-7 [R-(R*,S*)]-β-[[(1,1-Dimethylethoxy)carbonyl]-amino]-α-(2-furanyl)cyclohexanepropanol 
• 138448-19-8 (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester 
• 121533-54-8 (4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid 
• 115766-13-7 (S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-N-methoxy-N-methylcyclohexanepropanamide 
• 98105-42-1 (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal 
• 37736-82-6 (S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 104882-44-2 (2S,3S)-2-(tert-butoxycarboxamido)-1-cyclohexyl-5-hexen-3-ol 
• 124577-56-6 (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-5-<2-(mesyloxy)ethyl>-2,2-dimethyloxazolidine 
• 145341-80-6 (4S,5S)-3-(tert-butoxycarbonyl)-4-cyclohexylmethyl-5-formylmethyl-2,2-dimethyl-1,3-oxazolidine 
• 143122-11-6 (4S,5S)-5-allyl-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine 
• 124577-55-5 (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol 

Downstream Products

• 105852-64-0 (2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide 
• 129921-94-4 N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide 
• 124032-35-5 (2S,4S,5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-butylhexanamide 
• 123580-22-3 [(S)-2-Cyclohexyl-1-((2S,4R)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester 
• 124032-36-6 (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one 
• 124032-42-4 [(S)-2-Cyclohexyl-1-((S)-4-isopropyl-5-oxo-2,5-dihydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester 
• 141258-92-6 N-Butyl-2-[1-((4S,5S)-4-cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-meth-(Z)-ylidene]-3-methyl-butyramide 
• 141258-90-4 (4S,5S)-5-((Z)-2-Butylcarbamoyl-3-methyl-but-1-enyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 141258-93-7 (4S,5S)-4-Cyclohexylmethyl-5-((R)-2-methoxycarbonyl-3-methyl-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 141258-95-9 (4S,5S)-4-Cyclohexylmethyl-5-((S)-2-methoxycarbonyl-3-methyl-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 131316-86-4 (4S,5S)-5-((R)-2-Butylcarbamoyl-3-methyl-butyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 126259-92-5 t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-cyclobutylhydroxymethyl]-2,2-dimethyl-3-oxazolidinecarboxylate 
• 127230-21-1 Toluene-4-sulfonic acid (2S,4S,5R,6S)-7-cyclohexyl-4,5-dihydroxy-2-methyl-6-(toluene-4-sulfonylamino)-heptyl ester 
• 127230-19-7 (4S,5R)-4-Cyclohexylmethyl-5-((1S,3S)-1-hydroxy-4-methanesulfonyloxy-3-methyl-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Grignard addition to aldonitrones. Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols

A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4- diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from β- amino-α-hydroxy aldehydes followed by reduction of the resulting N- benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3- diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV- 1 protease inhibitors.

Enantioselective synthesis of N-Boc-2,2-dimethyloxazolidine-5-carbaldehydes, versatile precursors of dipeptide isosteres

Highly enantioenriched cis and trans N-Boc-2,2-dimethyl-oxazolidine-5-carbaldehydes have been efficiently prepared from N-Boc-3-amino-1,2-alkanediols, readily available in enantiopure or enantioenriched form by Sharpless epoxidation methodology. These compounds have been converted into N-Boc-(S)-γ-[(S)-1-aminoalkyl]-γ-lactones which are key intermediates of hydroxyethylene dipeptide isosteres.

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A stereoselective synthesis of an aminodiol derivative (dipeptide mimic) has been developed via iterative homologation of protonated cyclohexylalaninal (Dondoni reaction).