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(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID, also known as Boc-Asp(OtBu)-OH, is a chemical compound that serves as a crucial building block in peptide synthesis. It is a derivative of aspartic acid, featuring a tert-butoxycarbonyl (Boc) protecting group that shields the amino group during synthesis, and a diphenylsilyloxy group that protects the hydroxyl group. (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID plays a significant role in medicinal chemistry and drug development, enabling the creation of novel peptide-based drugs and facilitating the study of structure-activity relationships of peptide molecules in biological systems.

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  • 145790-51-8 Structure
  • Basic information

    1. Product Name: (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID
    2. Synonyms: (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID
    3. CAS NO:145790-51-8
    4. Molecular Formula: C24H33NO5Si
    5. Molecular Weight: 443.60802
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 145790-51-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 534 °C at 760 mmHg
    3. Flash Point: 276.7 °C
    4. Appearance: /
    5. Density: 1.12 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID(CAS DataBase Reference)
    10. NIST Chemistry Reference: (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID(145790-51-8)
    11. EPA Substance Registry System: (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID(145790-51-8)
  • 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: 145790-51-8(Hazardous Substances Data)

145790-51-8 Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID is used as a key intermediate in the synthesis of peptide-based drugs for various therapeutic applications. Its role in protecting the functional groups of aspartic acid allows for the controlled assembly of complex peptide structures, enhancing the development of innovative medications.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID is utilized as a valuable tool for studying the structure-activity relationships of peptide molecules. This understanding is essential for optimizing the pharmacological properties of peptide drugs, such as potency, selectivity, and stability.
Used in Drug Development:
(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILYLOXY)PROPANOIC ACID is employed in the development of new drugs, particularly in the design and synthesis of peptide therapeutics. Its protective groups enable the synthesis of peptides with specific functionalities and biological activities, contributing to the advancement of targeted and effective treatments for various diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 145790-51-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,5,7,9 and 0 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 145790-51:
(8*1)+(7*4)+(6*5)+(5*7)+(4*9)+(3*0)+(2*5)+(1*1)=148
148 % 10 = 8
So 145790-51-8 is a valid CAS Registry Number.

145790-51-8SDS

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 3-[tert-butyl(diphenyl)silyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

1.2 Other means of identification

Product number -
Other names -

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:145790-51-8 SDS

145790-51-8Relevant articles and documents

Tataricins A and B, two novel cyclotetrapeptides from Aster tataricus, and their absolute configuration assignment

Xu, Hui-Min,Yi, Hua,Zhou, Wen-Bing,He, Wen-Jun,Zeng, Gang-Zhi,Xu, Wen-Yan,Tan, Ning-Hua

, p. 1380 - 1383 (2013/04/23)

Two novel cyclotetrapeptides, tataricins A and B, with a unique cyclopeptide backbone and aδ 2,4Pro side chain, were isolated from the traditional Chinese medicine Aster tataricus. Their structures and absolute configurations were determined using a combination of spectroscopic data, the advanced Marfey's method, and a total synthesis. Copyright

Design, Synthesis, and invitro Antibacterial Activity of Fluoroquinolone Derivatives Containing a Chiral 3-(Alkoxyimino)-2-(aminomethyl)azetidine Moiety

Lv, Kai,Sun, Yexin,Sun, Lanyin,Wei, Zengquan,Guo, Huiyuan,Wu, Jinwei,Liu, Mingliang

experimental part, p. 1230 - 1236 (2012/08/08)

A series of novel (R)/(S)-7-(3-alkoxyimino-2-aminomethyl-1-azetidinyl)fluoroquinolone derivatives were synthesized and evaluated for their invitro antibacterial activity against representative strains. Our results reveal that 12 of the target compounds generally show better activity (MIC: -1) against the tested Gram-positive strains including MRSA and MRSE than levofloxacin (LVFX, MIC: 0.125-8μgmL-1). Their activity is similar to that of gemifloxacin (GMFX, MIC: -1). However, they are generally less active than the two reference drugs against Gram-negative strains. Moreover, against clinical strains of S.aureus including MRSA and S.epidermidis including MRSE, the MIC50 values (0.06-16μgmL-1) and MIC90 values (0.5-32μgmL-1) of compounds 16w, y, and z are 2-8- and 2-16-fold less than LVFX, respectively, and 16w (MIC90 range: 0.5-4μgmL-1) was also found to be more active than GMFX (MIC90 range: 1-8μgmL-1).

Novel orally active morpholine N-arylsulfonamides γ-secretase inhibitors with low CYP 3A4 liability

Josien, Hubert,Bara, Thomas,Rajagopalan, Murali,Clader, John W.,Greenlee, William J.,Favreau, Leonard,Hyde, Lynn A.,Nomeir, Amin A.,Parker, Eric M.,Song, Lixin,Zhang, Lili,Zhang, Qi

scheme or table, p. 6032 - 6037 (2010/05/18)

A new class of 2,6-disubstituted morpholine N-arylsulfonamide γ-secretase inhibitors was designed based on the introduction of a morpholine core in lieu or piperidine in our lead series. This resulted in compounds with improved CYP 3A4 profiles. Several a

Concise total synthesis of the thiazolyl peptide antibiotic GE2270 A

Delgado, Oscar,Martin Mueller,Bach, Thorsten

supporting information; experimental part, p. 2322 - 2339 (2009/04/10)

The potent antibiotic thiazolylpeptide GE2270 A was synthesized starting from N-tert-butyloxycarbonyl protected valine in a longest linear sequence of 20 steps and with an overall yield of 4.8 %. Key strategy was the assembly of the 2,3,6-trisubstituted p

SUBSTITUTED N-ARYLSULFONYLHETEROCYCLIC AMINES AS GAMMA-SECRETASE INHIBITORS

-

Page/Page column 66, (2010/02/15)

This invention discloses novel gamma secretase inhibitors of the formula I: wherein: L is -O- , -N(R6)-, -S-, -S(O)-, or -S(O2)-; R1 is selected from the group consisting of aryl and heteroaryl; R2 is selected f

Asymmetric synthesis of cis-2,4-disubstituted azetidin-3-ones from metal carbene chemistry

Burtoloso, Antonio Carlos B.,Correia, Carlos Roque D.

, p. 5636 - 5646 (2007/10/03)

Several chiral cis-2,4-disubstituted azetidin-3-ones were prepared as single diastereoisomers from N-protected amino acids, employing a highly stereoselective copper carbenoid N-H insertion reaction of diazoketones. These azetidin-3-ones were then convert

Chirality transfer in the aza-[2,3]-Wittig sigmatropic rearrangement

Anderson, James C.,Gair Ford,Whiting, Matthew

, p. 3734 - 3748 (2007/10/03)

The aza-[2,3]-Wittig sigmatropic rearrangements of substrates derived from enantiomerically pure alanine, valine and serine with phenyl and ester anion stabilising groups were investigated for their efficiency in chirality transfer. It was found that a me

Metal carbene N-H insertion of chiral α, α′-dialkyl α-diazoketones. A novel and concise method for the stereocontrolled synthesis of fully substituted azetidines

Burtoloso, Antonio Carlos B.,Correia, Carlos Roque D.

, p. 3355 - 3358 (2007/10/03)

The syntheses of all cis substituted azetidines were accomplished in few steps from L-serine in modest to high yields. The key step was based on a rhodium or copper carbenoid N-H insertion of α,α′- dialkyl-α-diazoketones to furnish cis-2,4-dial

Protection of Hydroxy Groups by Silylation: Use in Peptide Synthesis and as Lipophilicity Modifiers for Peptides

Davies, John S.,Higginbotham, Clement L.,Tremeer, E. John,Brown, Charles,Treadgold, Richard C.

, p. 3043 - 3048 (2007/10/02)

A survey of a series of organosilyl derivatives of serine and tyrosine has shown that they have a satisfactory stability profile for use in peptide synthesis.Only when alkaline conditions were used did side-reactions appear.A range of stability profiles have been determined from a study of organosilyl derivatised dipetides under different conditions, giving t1/2 values for hydrolysis ranging from 41 to 465 min in acid conditions, yet giving long-term stability at pH-values near to neutrality.

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