77171-41-6

Basic information

• Product Name: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID
• Synonyms: N-BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID;N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID;BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC ACID;BOC-(2R,3R)-APNS-OH;BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID;(2R,3R)-3-(BOC-AMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID;(2R,3R)-3-(boc-Amino)-2-hydroxy-4-phenylbutricacid;Boc-(2R,3R)-AHPA,
• CAS NO: 77171-41-6
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• Mol File: 77171-41-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 499.1°C at 760 mmHg
• Flash Point: 255.7°C
• Appearance: /
• Density: 1.215g/cm³
• Vapor Pressure: 8.81E-11mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: ?20°C
• PKA: 3.57±0.17(Predicted)
• BRN: 8993437
• CAS DataBase Reference: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(77171-41-6)
• EPA Substance Registry System: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(77171-41-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 77171-41-6(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(20)16-11(12(17)13(18)19)9-10-7-5-4-6-8-10/h4-8,11-12,17H,9H2,1-3H3,(H,16,20)(H,18,19)/t11-,12-/m0/s1

Upstream product

• 116565-03-8 N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 290836-37-2 (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone 
• 290836-34-9 (3S)-1,1-dibromo-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 147915-02-4 (2S,3S)-3-amino-4-phenylbutane-1,2-diol 
• 200616-22-4 (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol 
• 62023-61-4 (2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid 
• 773837-37-9 sodium cyanide 
• 18942-49-9 Boc-D-Phe-OH 
• 1275576-32-3 C₁₅H₂₃NO₄ 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Downstream Products

• 145986-90-9 N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester 
• 521275-21-8 carbonic acid 1-{N-benzyl-N'-[(2,6-dimethyl-phenoxy)-acetyl]-hydrazinocarbonyl}-2-tert-butoxycarbonylamino-3-phenyl-propyl ester isobutyl ester 
• 521275-20-7 acetic acid 3-[N'-benzyl-N'-(3-tert-butoxycarbonylamino-2-isobutoxycarbonyloxy-4-phenyl-butyryl)-hydrazinocarbonyl]-2-methyl-phenyl ester 
• 602319-14-2 (1S,2S)-2-[(tert-butoxycarbonyl)amino]-1-[(cyclohexyloxy)carbonyl]-3-phenylpropyl benzoate 
• 186538-14-7 (R)-N-(2-methylbenzyl)-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 
• 226997-99-5 (R)-N-benzyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 
• 226998-01-2 (R)-N-(3-methylbenzyl)-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 
• 226998-03-4 (R)-N-(4-methylbenzyl)-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 
• 226997-95-1 (R)-N-(2,6-dimethylbenzyl)-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 
• 1053653-19-2 Acetic acid 3-[(1S,2S)-1-benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-phenyl ester 
• 1053258-94-8 Acetic acid 3-[(1S,2S)-1-benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-methyl-phenyl ester 

Relevant articles and documents

A ubenimex novel synthesis process

The invention discloses a novel synthesis process of ubenimex. The synthesis process comprises the following steps: enabling a raw material, namely (2S,3R)-3-amino-2-hydroxy-4-phenyl butyric acid, to react with di-tert-butyl dicarbonate ester so as to prepare an intermediate I, wherein di-tert-butyl dicarbonate ester is added in multiple batches; reacting the intermediate I with L-leucine tert-butyl ester hydrochloride so as to obtain an intermediate II, wherein L-leucine tert-butyl ester hydrochloride is preferred and is conducive to the improvement of yield and purity of the intermediate II; and respectively removing protecting groups, namely tert-butyloxy carbonyl and tert-butyl ester, of the intermediate II in an acid-base system, wherein through the operation, the protecting groups are effectively removed by regulating pH value by virtue of the acid-base system, so that the yield and purity of the finished ubenimex are improved.

Design and synthesis of several small-size HTLV-I protease inhibitors with different hydrophilicity profiles

The human T cell leukemia/lymphotropic virus type 1 (HTLV-I) is clinically associated with adult T cell leukemia/lymphoma, HTLV-I associated myelopathy/tropical spastic paraparesis, and a number of other chronic inflammatory diseases. To stop the replication of the virus, we developed highly potent tetrapeptidic HTLV-I protease inhibitors. In a recent X-ray crystallography study, several of our inhibitors could not form co-crystal complexes with the protease due to their high hydrophobicity. In the current study, we designed, synthesized and evaluated the HTLV-I protease inhibition potency of compounds with hydrophilic end-capping moieties with the aim of improving pharmaceutic and pharmacokinetic properties.

A practical and convenient synthesis of the protease inhibitor epibestatin

A convenient synthesis of the protease inhibitor epibestatin, a useful component in protease inhibition cocktails for use in proteomics research, is described. The synthesis sequence consists of seven steps, starting from phenylacetaldehyde, yielding enantiopure epibestatin in 8% overall yield. A regioselective Mitsunobu transformation of a diol is the key step in the sequence. Georg Thieme Verlag Stuttgart.