98737-29-2

Basic information

• Product Name: (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane
• Synonyms: tert-Butyl [(S)-1-[(S)-Oxiran-2-yl]-2-phenylethyl]carbamate (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane;(2R,3S)-1,2-Epoxy-3-(Boc-aMino)-4-phenylbutane, 95+%;(2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane 99%;(2S,3S)-3-Boc-amino-1,2-epoxy-4-phenylbutane, >=99%;3S)-1;(2S,3S)-1,2-EPOXY-3-(BOC-AMINO)-4-PHENY&;[(1S)-1-((2S)-Oxiranyl)-2-phenylethyl]carbamicac;(2S, 3S)-3-(t-Butoxy Carbonyl Amino)-4-Phenyl-1,2-Epoxy-Butane
• CAS NO: 98737-29-2
• Molecular Formula: C15H21NO3
• Molecular Weight: 263.33
• EINECS: 425-420-5
• Product Categories: chiral;API intermediates;Aromatics Compounds;Aromatics;Chiral Reagents;Heterocycles
• Mol File: 98737-29-2.mol
• Article Data: 202

Chemical Properties

• Melting Point: 125-127 °C(lit.)
• Boiling Point: 398.837 °C at 760 mmHg
• Flash Point: 195.01 °C
• Appearance: off-white solid
• Density: 1.118 1.118 g/cm^>3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 12.19±0.46(Predicted)
• Water Solubility: Insoluble in water. Soluble in Chloroform, Dichloromethane and Ethyl Acetate.
• CAS DataBase Reference: (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane(98737-29-2)
• EPA Substance Registry System: (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane(98737-29-2)

Safety Data

• Hazard Codes: F,Xi,N
• Statements: 10-36/37/38-50/53
• Safety Statements: 7/9-16-26-36/37/39-61-60
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 98737-29-2(Hazardous Substances Data)

Usage

Description

(2S,3S)-1,2-Epoxy-3-(boc-amino)-4-phenylbutane is a chiral off-white solid that serves as a crucial building block in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable intermediate in the development of drugs targeting HIV-1 protease inhibitors, as well as in the creation of (hydroxyethyl)urea peptidomimetics and arylsulfonamides with anti-HIV activity.

Uses

Used in Pharmaceutical Industry:
(2S,3S)-1,2-Epoxy-3-(boc-amino)-4-phenylbutane is used as a key intermediate in the synthesis of HIV-1 protease inhibitors. Its chiral structure plays a vital role in the development of these inhibitors, which are essential in the treatment of HIV/AIDS.
Used in Medicinal Chemistry:
(2S,3S)-1,2-Epoxy-3-(boc-amino)-4-phenylbutane is employed as a building block in the synthesis of (hydroxyethyl)urea peptidomimetics and arylsulfonamides with anti-HIV activity. These compounds have the potential to offer new therapeutic options for the treatment of HIV/AIDS.
Used in Enantiomer Synthesis:
As an enantiomerically pure compound, (2S,3S)-1,2-Epoxy-3-(boc-amino)-4-phenylbutane is used in the synthesis of enantiomer S. Atazanavir intermediate, which is an important component in the production of Atazanavir, an antiretroviral medication used to treat HIV/AIDS.

InChI:InChI=1/C15H21NO3/c1-15(2,3)19-14(17)16-12(13-10-18-13)9-11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,16,17)/t12-,13-/m0/s1

Upstream product

• 6814-64-8 methylenedimethyl sulfurane 
• 72155-45-4 Boc-L-phenylalaninal 
• 103127-52-2 ((S)-1-benzylallyl)carbamic acid tert-butyl ester 
• 165727-45-7 tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 102123-74-0 (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 108860-11-3 [1-(2-chloro-1-hydroxy-ethyl)-3-methyl-butyl]-carbamic acid tert-butyl ester 
• 1174892-47-7 C₂₂H₃₉NO₆SSi 
• 110-05-4 di-tert-butyl peroxide 
• 3395-74-2 1-((benzyloxy)methyl)-4-(tert-butyl)benzene 
• 98-51-1 4-tert-butyltoluene 
• 124-38-9 carbon dioxide 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 22201-45-2 p-t-butyl benzoic acid anhydride 

Downstream Products

• 142694-73-3 N-<1-phenyl-2(S)-<(tert-butoxycarbonyl)amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide 
• 142580-65-2 [(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 
• 142580-69-6 {(1S,2R)-1-Benzyl-2-hydroxy-3-[(S)-1-((S)-2-hydroxy-1-phenyl-ethylcarbamoyl)-2-phenyl-ethylamino]-propyl}-carbamic acid tert-butyl ester 
• 142580-66-3 {(1S,2R)-1-Benzyl-2-hydroxy-3-[(3S,4aS,8aS)-3-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-octahydro-isoquinolin-2-yl]-propyl}-carbamic acid tert-butyl ester 
• 142580-68-5 {(1S,2R)-1-Benzyl-2-hydroxy-3-[2-hydroxy-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethylamino]-propyl}-carbamic acid tert-butyl ester 
• 142694-72-2 {(1S,2R)-1-Benzyl-2-hydroxy-3-[(R)-1-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethylamino]-propyl}-carbamic acid tert-butyl ester 
• 251105-80-3 N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride 
• 184357-17-3 1,1-dimethylethyl [(1S,2R)-3-[(cyclohexylmethyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamate 
• 190508-37-3 (2S,4R)-1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-4-(pyridin-4-ylmethoxy)-piperidine-2-carboxylic acid tert-butylamide 
• 190712-45-9 [(1S,2R)-1-Benzyl-3-(2-tert-butylcarbamoyl-phenylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 
• 171858-52-9 (2R,3S,11'S,8'S)-3-(tert-butoxycarbonylamino)-4-phenyl-1-<<7',10'-dioxo-8'-(1-methylpropyl)-2'-oxa-6',9'-diazabicyclo<11.2.2>heptadeca-13',15',16'-trien-11'-yl>amino>butan-2-ol 
• 162538-06-9 {(1S,2R)-1-Benzyl-3-[benzyl-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-amino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 162536-41-6 (2R,3S)-1-(benzylamino)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol 
• 160232-54-2 1,1-dimethylethyl [(1S,2R)-2-hydroxy-3-(methylamino)-1-(phenylmethyl)propyl]carbamate 

Relevant articles and documents

One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence

Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.

Combining photoredox catalysis and oxoammonium cations for the oxidation of aromatic alcohols to carboxylic acids

A methodology is reported for converting alcohols to the corresponding carboxylic acids. A dual catalytic system involving a merger of photoredox catalysis and 4-acetamido-TEMPO is employed to carry out this oxidation process.

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.