1009093-14-4

Basic information

• Product Name: N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester
• Synonyms: N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester;((1R,2R)-2-Hydroxy-1-hydroxymethyl-2-phenylethyl)carbamic acid tert-butyl ester
• CAS NO: 1009093-14-4
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.32084
• Product Categories: Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1009093-14-4.mol

Chemical Properties

• Boiling Point: 453.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.163±0.06 g/cm3(Predicted)
• PKA: 11?+-.0.46(Predicted)
• CAS DataBase Reference: N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester(1009093-14-4)
• EPA Substance Registry System: N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester(1009093-14-4)

Safety Data

• Hazardous Substances Data: 1009093-14-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly in the preparation of Puromycin and its derivatives. Its unique structural features allow it to serve as a building block for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester is utilized as a versatile reagent for the preparation of a wide range of organic compounds. Its ability to undergo various chemical reactions, such as esterification, amidation, and substitution, makes it a valuable component in the synthesis of complex organic molecules.
Used in Research and Development:
N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester is also employed in research and development settings, where it can be used to study the effects of stereochemistry on the properties and reactivity of organic compounds. Its unique structure provides a platform for exploring new reaction pathways and developing innovative synthetic methods.

Upstream product

• 217661-62-6 [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 46032-98-8 (1R,2R)-2-amino-1-phenylpropane-1,3-diol 
• 185692-85-7 tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl carbamate 
• 488727-71-5 (4R)-(1-hydroxy-phenyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 217661-64-8 Acetic acid (1R,2R)-3-acetoxy-2-tert-butoxycarbonylamino-1-phenyl-propyl ester 
• 528523-46-8 tert-butyl (1R,2R)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate 
• 528523-48-0 tert-butyl (4R,5S)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate 
• 528523-53-7 tert-butyl (4R,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate 
• 528523-51-5 (4R,5S)-4-[(S)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 528523-47-9 tert-butyl (1R,2S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate 
• 528523-57-1 diethyl (3R,4S)-1,1-difluoro-4-hydroxy-3-([pentadecylcarbonyl]amino)-4-phenylbutylphosphonate 
• 528523-55-9 diethyl (2S,3R,4S)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate 
• 56-75-7 chloramphenicol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 439797-74-7 (1R,2R)-1,3-diacetoxy-2-amino-1-phenyl-propane 
• 111136-67-5 (1R,2R)-2-acetamido-1-phenylpropane-1,3-diyl diacetate 

Relevant articles and documents

Synthetic Studies Toward the Skyllamycins: Total Synthesis and Generation of Simplified Analogues

Herein, we report our synthetic studies toward the skyllamycins, a highly modified class of nonribosomal peptide natural products which contain a number of interesting structural features, including the extremely rare α-OH-glycine residue. Before embarking on the synthesis of the natural products, we prepared four structurally simpler analogues. Access to both the analogues and the natural products first required the synthesis of a number of nonproteinogenic amino acids, including three β-OH amino acids that were accessed from the convenient chiral precursor Garner's aldehyde. Following the preparation of the suitably protected nonproteinogenic amino acids, the skyllamycin analogues were assembled using a solid-phase synthetic route followed by a final stage solution-phase cyclization reaction. To access the natural products (skyllamycins A-C) the synthetic route used for the analogues was modified. Specifically, linear peptide precursors containing a C-terminal amide were synthesized via solid-phase peptide synthesis. After cleavage from the resin the N-terminal serine residue was oxidatively cleaved to a glyoxyamide moiety. The target natural products, skyllamycins A-C, were successfully prepared via a final step cyclization with concomitant formation of the unusual α-OH-glycine residue. Purification and spectroscopic comparison to the authentic isolated material confirmed the identity of the synthetic natural products.

AZAQUINAZOLINE INHIBITORS OF ATYPICAL PROTEIN KINASE C

The present invention provides a compound of formula (I) or a salt thereof, wherein R7, R8, R9, G, and X are as defined herein. A compound of formula (I) and its salts have a PKC inhibitory activity, and may be used to treat proliferative disorders.

Iron(II)-catalyzed intramolecular aminohydroxylation of olefins with functionalized hydroxylamines

A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral iron(II) complexes and preliminary mechanistic studies reveal an iron nitrenoid is a possible intermediate that can undergo either aminohydroxylation or aziridination, and the selectivity can be controlled by careful selection of counteranion/ligand combinations.

Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenation

An efficient preparation of highly enantiomerically enriched aryl β-hydroxy α-amino esters via dynamic kinetic resolution (DKR), asymmetric transfer hydrogenation of α-amino β-keto esters is described. The anti β-hydroxyl α-amino esters were obtained both in high yields and high diasteroselectivity. The observed high anti selectivity is inconsistent with the previous results in literature. The absolute stereochemistry of the aryl β-hydroxy α-amino esters was unambiguously confirmed via chemical derivatization as well as Vibrational Circular Dichroism (VCD) techniques.

Synthesis of a fluorine-substituted puromycin derivative for Bronsted studies of ribosomal-catalyzed peptide bond formation

The mechanism by which the ribosome catalyzes peptide bond formation remains controversial. Here we describe the synthesis of a nucleoside that can be used in Bronsted experiments to assess the transition state of ribosome catalyzed peptide bond formation. This substrate is the nucleoside 3 -amino-3 -deoxy-3 -[(3 R)-3-fluoro-L-phenyl-alanyl]-N6,N 6-dimethyladenosine, which was prepared from (1R,2R)-2-amino-1- phenylpropane-1,3-diol. This substrate is active in peptide bond formation on the ribosome and is a useful probe for Bronsted analysis experiments on the ribosome.

Compounds and Methods for Inhibiting the Interaction of BCL Proteins with Binding Partners

The invention relates to isoxazolidine containing compounds that bind to bcl proteins and inhibit Bcl function. The compounds may be used for treating and modulating disorders associated with hyperproliferation, such as cancer.

Synthesis and biological properties of novel sphingosine derivatives

Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from l-serine or (1S,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(1S,2R)-2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors.

Synthesis of non-competitive inhibitors of sphingomyelinases with significant activity

A series of short-chain analogues of N-palmitoylsphingosine-1-phosphate, modified by replacement of the phosphate and the long alkenyl side chain with hydrolytically stable difluoromethylene phosphonate and phenyl, respectively, were prepared to study the structure-activity relationship for inhibition of sphingomyelinase. The study revealed that inhibition is highly dependent upon the stereochemistry of the asymmetric centers of the acylamino moiety, and resulted in identification of a non-competitive inhibitor with the same level of inhibitory activity of schyphostatin, the most potent of the few known small molecular inhibitors of sphingomyelinase.

Stereoselective synthesis of chloramphenicol from D-serine

An efficient synthesis of the widely used antibiotic chloramphenicol (1) is described. The key step in the synthesis involves chelation-controlled addition of phenylmagnesium bromide to a suitably protected D-serinal derivative, affording the pivotal D-threo 1,2-amino alcohol intermediate 3 in a highly stereoselective manner.