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
• Article Data: 9

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

Description

N-[(1R,2R)-2-Hydroxy-1-(hydroxyMethyl)-2-phenylethyl]carbaMic Acid tert-Butyl Ester is a complex organic compound characterized by its pale yellow oil appearance. It is a carbamic acid derivative with a specific stereochemistry at the 1R,2R configuration, featuring a hydroxyl group and a hydroxymethyl group attached to a phenylethyl moiety. The tert-butyl ester group further modifies its chemical properties, making it a versatile intermediate in organic synthesis.

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.

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.

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.