62023-65-8

Basic information

• Product Name: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID
• Synonyms: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID;(2S,3R)-3-(BOC-AMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID;BOC-(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC ACID;BOC-(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID;BOC-(2S,3R)-APNS-OH;N-tert-BOC-[2S,3R]-3-amino-2-hydroxy-4-phenylbutyric acid;Boc-(2S,3R)-AHPA,
• CAS NO: 62023-65-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• Mol File: 62023-65-8.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 499.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 3.57±0.17(Predicted)
• Water Solubility: Insoluble in water. Soluble in organic solvents.
• BRN: 5909790
• CAS DataBase Reference: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(62023-65-8)
• EPA Substance Registry System: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(62023-65-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 62023-65-8(Hazardous Substances Data)

Usage

Description

N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is a novel protected amino acid that plays a crucial role in the synthesis of bestatin and its analogs. It is characterized by its unique molecular structure, which includes a Boc-protected 3-amino group, a 2-hydroxy group, and a 4-phenylbutyric acid backbone. N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is essential for the development of pharmaceuticals and bioactive molecules with potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is used as a key intermediate in the synthesis of bestatin and its analogs for the pharmaceutical industry. Bestatin is a natural product with immunomodulatory, antitumor, and protease inhibitory properties. Its analogs have been developed to enhance these properties and explore their potential in treating various diseases.
Used in Biochemical Research:
N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is used as a protected amino acid in biochemical research for the development of novel peptides, peptidomimetics, and other bioactive molecules. The Boc protection group allows for selective deprotection and coupling reactions, enabling the synthesis of complex molecular structures with specific biological activities.
Used in Drug Discovery:
N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is used as a building block in drug discovery for the design and synthesis of new pharmaceutical agents. Its unique structure and functional groups can be exploited to create molecules with improved pharmacokinetic and pharmacodynamic properties, leading to the development of more effective and safer drugs.

Upstream product

• 81926-51-4 N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 116565-03-8 N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 773837-37-9 sodium cyanide 
• 18942-49-9 Boc-D-Phe-OH 
• 59554-14-2 (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid 
• 1275576-32-3 C₁₅H₂₃NO₄ 
• 77119-85-8 N-(tert-butoxycarbonyl)-D-phenylalaninal 
• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 223763-61-9 (4R,5S)-5-benzyl-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one 
• 95832-37-4 (4R,5S)-5-benzyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one 

Downstream Products

• 1054684-42-2 ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester 
• 147318-83-0 [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 246506-79-6 (S)-benzyl 2-((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanamido)-4-methylpentanoate 
• 359691-63-7 (S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-5,5-dimethyl-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester 
• 359691-66-0 (S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester 
• 144069-71-6 [1-benzyl-3-(2-tert-butylcarbamoyl-piperidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 160470-73-5 Apstatin 
• 177355-09-8 [(1S,2S)-1-Benzyl-3-((2S,4S)-2-tert-butylcarbamoyl-4-chloro-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 478699-11-5 {(1S,2S)-1-Benzyl-3-[(R)-4-(2-chloro-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 478699-59-1 Boc-Apns-Dmt-NH(o-methylbenzyl) 
• 159000-71-2 Boc-Apns-Dmt-NHtBu 
• 145986-90-9 N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester 
• 1271772-86-1 C₃₄H₅₀F₂N₄O₆ 

Relevant articles and documents

Design, synthesis and biological evaluation of hybrid of ubenimex-fluorouracil for hepatocellular carcinoma therapy

In our previous study, we discovered a ubenimex-fluorouracil (5FU) conjugates BC-02, which displays significant in vivo anti-tumor activity, however, the instability of BC-02 in plasma limits its further development as a drug candidate. Herein, we designe

(2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative as well as preparation method and application thereof

The invention discloses a (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative shown as a formula (I) or an optical isomer, a diastereomer and racemate mixture and pharmaceutically acceptable salt thereof as well as a preparation method and application of the (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative. It is shown by comparison of results of a positive control group and a model group on lymphedema prevention experiments that the compound disclosed in the invention shows obvious anti-edema activity.

TUBULIN BINDING AGENTS

The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.