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TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 149451-80-9 Structure
  • Basic information

    1. Product Name: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE
    2. Synonyms: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE
    3. CAS NO:149451-80-9
    4. Molecular Formula: C15H23NO4
    5. Molecular Weight: 281.35
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 149451-80-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE(CAS DataBase Reference)
    10. NIST Chemistry Reference: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE(149451-80-9)
    11. EPA Substance Registry System: TERT-BUTYL [(1S,2S)-1-BENZYL-2,3-DIHYDROXYPROPYL]CARBAMATE(149451-80-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 149451-80-9(Hazardous Substances Data)

149451-80-9 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 149451-80-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,9,4,5 and 1 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 149451-80:
(8*1)+(7*4)+(6*9)+(5*4)+(4*5)+(3*1)+(2*8)+(1*0)=149
149 % 10 = 9
So 149451-80-9 is a valid CAS Registry Number.

149451-80-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyl N-(3,4-dihydroxy-1-phenylbutan-2-yl)carbamate

1.2 Other means of identification

Product number -
Other names Carbamic acid,N-[(1S,2S)-2,3-dihydroxy-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:149451-80-9 SDS

149451-80-9Relevant articles and documents

Peptidomimetic plasmepsin inhibitors with potent anti-malarial activity and selectivity against cathepsin D

Zogota, Rimants,Kinena, Linda,Withers-Martinez, Chrislaine,Blackman, Michael J.,Bobrovs, Raitis,Pantelejevs, Teodors,Kanepe-Lapsa, Iveta,Ozola, Vita,Jaudzems, Kristaps,Suna, Edgars,Jirgensons, Aigars

supporting information, p. 344 - 352 (2018/12/11)

Following up the open initiative of anti-malarial drug discovery, a GlaxoSmithKline (GSK) phenotypic screening hit was developed to generate hydroxyethylamine based plasmepsin (Plm) inhibitors exhibiting growth inhibition of the malaria parasite Plasmodium falciparum at nanomolar concentrations. Lead optimization studies were performed with the aim of improving Plm inhibition selectivity versus the related human aspartic protease cathepsin D (Cat D). Optimization studies were performed using Plm IV as a readily accessible model protein, the inhibition of which correlates with anti-malarial activity. Guided by sequence alignment of Plms and Cat D, selectivity-inducing structural motifs were modified in the S3 and S4 sub-pocket occupying substituents of the hydroxyethylamine inhibitors. This resulted in potent anti-malarials with an up to 50-fold Plm IV/Cat D selectivity factor. More detailed investigation of the mechanism of action of the selected compounds revealed that they inhibit maturation of the P. falciparum subtilisin-like protease SUB1, and also inhibit parasite egress from erythrocytes. Our results indicate that the anti-malarial activity of the compounds is linked to inhibition of the SUB1 maturase plasmepsin subtype Plm X.

Plasmepsin inhibitory activity and structure-guided optimization of a potent hydroxyethylamine-based antimalarial hit

Jaudzems, Kristaps,Tars, Kaspars,Maurops, Gundars,Ivdra, Natalija,Otikovs, Martins,Leitans, Janis,Kanepe-Lapsa, Iveta,Domraceva, Ilona,Mutule, Ilze,Trapencieris, Peteris,Blackman, Michael J.,Jirgensons, Aigars

, p. 373 - 377 (2014/05/06)

Antimalarial hit 1SR (TCMDC-134674) identified in a GlaxoSmithKline cell based screening campaign was evaluated for inhibitory activity against the digestive vacuole plasmepsins (Plm I, II, and IV). It was found to be a potent Plm IV inhibitor with no selectivity over Cathepsin D. A cocrystal structure of 1SR bound to Plm II was solved, providing structural insight for the design of more potent and selective analogues. Structure-guided optimization led to the identification of structurally simplified analogues 17 and 18 as low nanomolar inhibitors of both, plasmepsin Plm IV activity and P. falciparum growth in erythrocytes.

PROCESS FOR REDUCTION OF ALPHA-ACYLOXY SULFIDE DERIVATIVES

-

, (2012/09/10)

The present invention provides an efficient and scalable process to prepare the compound of formula 4 by reduction of the corresponding α-acyloxy sulfides.

Asymmetric synthesis of amines by the knochel-type MgCl2- enhanced addition of benzyl zinc reagents to N -tert -Butanesulfinyl aldimines

Buesking, Andrew W.,Baguley, Tyler D.,Ellman, Jonathan A.

, p. 964 - 967 (2011/04/26)

The MgCl2-enhanced addition of benzyl zinc reagents to N-tert-butanesulfinyl imines proceeds readily at room temperature to afford the N-tert-butanesulfinyl-protected amine products in good yields and diastereomeric ratios. This method is functional group tolerant in both the imine substrate and benzyl zinc coupling partner. Moreover, benzyl zinc reagent addition to the N-tert-butanesulfinyl imine 3o prepared from isopropylidene-protected glyceraldehyde proceeds in high yield and with exceptional selectivity to provide rapid entry to hydroxyethylamine-based aspartyl protease inhibitors.(Figure Presented)

Synthesis and biological evaluation of novel allophenylnorstatine-based HIV-1 protease inhibitors incorporating high affinity P2-ligands

Ghosh, Arun K.,Gemma, Sandra,Simoni, Elena,Baldridge, Abigail,Walters, D. Eric,Ide, Kazuhiko,Tojo, Yasushi,Koh, Yasuhiro,Amano, Masayuki,Mitsuya, Hiroaki

scheme or table, p. 1241 - 1246 (2010/06/15)

A series of stereochemically defined cyclic ethers as P2-ligands were incorporated in an allophenylnorstatine-based isostere to provide a new series of HIV-1 protease inhibitors. Inhibitors 3b and 3c, containing conformationally constrained cyclic ethers,

Expedient asymmetric synthesis of (2S,3S)-Boc-phenylalanine epoxide, a key intermediate for the synthesis of biologically active compounds

Badorrey, Ramon,Diaz-de-Villegas, Maria D.,Galvez, Jose A.

experimental part, p. 2226 - 2229 (2010/03/03)

The asymmetric synthesis of (2S,3S)-3-(tert-butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane [(2S,3S)-Boc-phenylalanine epoxide] has been achieved in six steps and in 55% overall yield from the N-benzylimine derived from (R)-2,3-O-isopropylidene-glyceraldehy

Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones

Pico, Anna,Moyano, Albert,Pericas, Miquel A.

, p. 5075 - 5083 (2007/10/03)

A set of diversely substituted N-Boc-γ-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of α-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given γ-amino vinyl sulfone can be obtained with equal ease.

Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors

-

Page column 43, (2008/06/13)

Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

Ikunaka, Masaya,Matsumoto, Jun,Nishimoto, Yukifumi

, p. 1201 - 1208 (2007/10/03)

Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an α-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (±)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (±)-8b in 46% yield for another round of the enzymatic processing.

A totally stereocontrolled route to N-methyl-γ-amino-β-hydroxy acids: Asymmetric synthesis of the amino acid component of hapalosin

Catasus, Monica,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni

, p. 9309 - 9312 (2007/10/03)

A new approach to the synthesis of N-methyl-γ-amino-β-hydroxy acids, compounds that are essential components of several depsipeptides exhibiting highly interesting therapeutic profiles, is presented. Relevant steps in the synthetic sequence involve the totally stereoselective preparation of a protected aminoalkyl epoxide from a highly enantiopure 2,3-epoxy alcohol, efficient N-methylation and three-step conversion to the desired N-methyl amino acid. The method is exemplified by the enantioselective synthesis of (3R,4S)-4-(N-methylamino)-3-hydroxy-5-phenylpentanoic acid in two differently protected forms.

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