13500-53-3

Basic information

• Product Name: （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine
• Synonyms: （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine;(2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate;(2S,4R)-4-hydroxy-1,2-Pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl) ester
• CAS NO: 13500-53-3
• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.388
• Mol File: 13500-53-3.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 517.884 °C at 760 mmHg
• Flash Point: 267.007 °C
• Appearance: /
• Density: 1.3 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: 2-8°C
• CAS DataBase Reference: （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine(13500-53-3)
• EPA Substance Registry System: （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine(13500-53-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13500-53-3(Hazardous Substances Data)

Usage

General Description

(2S,4R)-1,2-dicarbobenzyloxy-4-hydroxypyrrolidine, also known as DBOH, is a chemical compound that belongs to the class of pyrrolidine derivatives. It is commonly used as a chiral building block in organic synthesis and pharmaceutical research. DBOH has two chiral centers, with the (2S,4R) configuration being the most common form. （2s，4r）-1，2-dicarbobenzyloxy-4-hydroxypyrrolidine is widely utilized in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals due to its versatile reactivity and ability to form a variety of complex structures. Additionally, DBOH has shown potential as a key intermediate in the production of various biologically active compounds, making it a valuable tool in the field of medicinal chemistry.

InChI:InChI=1/C20H21NO5/c22-17-11-18(19(23)25-13-15-7-3-1-4-8-15)21(12-17)20(24)26-14-16-9-5-2-6-10-16/h1-10,17-18,22H,11-14H2/t17-,18+/m1/s1

Upstream product

• 100-44-7 benzyl chloride 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 100-39-0 benzyl bromide 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 
• 501-53-1 benzyl chloroformate 
• 51-35-4 4-hydroxyproline 
• 2584-71-6 cis-hydroxy-D-proline 
• 51-35-4 4R-4-hydroxyproline 
• 100-51-6 benzyl alcohol 
• 541-41-3 chloroformic acid ethyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 88501-00-2 (2S,4R)-4-hydroxyproline benzyl ester p-toluenesulfonate 

Downstream Products

• 159551-87-8 (2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester 
• 159551-89-0 (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester 
• 159551-88-9 dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate 
• 159651-34-0 (1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 159551-90-3 (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 202473-18-5 (2S,3S,4R)-3-hydroxy-4-aminoproline 
• 202473-18-5 (2S,3R,4S)-3-hydroxy-4-aminoproline 
• 654083-19-9 (2S,3RS,4SR)-3,4-dihydroxyproline 
• 202473-19-6 (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester 
• 202473-20-9 (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester 
• 202473-13-0 (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester 
• 180297-93-2 3-O-benzyl-5,6-O-isopropylidene-2-O-[(2S,4R)-1,2-pyrrolidinedicarboxylic acid 1,2-dibenzylester-4-benzylphosphonooxy]-L-ascorbic acid 
• 1032958-69-2 (2S,4R)-N-benzyloxycarbonyl-4-myristoyloxypyrrolidine-2-carboxylic acid benzyl ester 
• 1032958-66-9 (2S,4R)-N-benzyloxycarbonyl-4-octanoyloxypyrrolidine-2-carboxylic acid benzyl ester 

Relevant articles and documents

Investigation of pH-dependent collagen triple-helix formation

(Figure Presented) Helices on demand: Collagen peptides were engineered to form triple helices under environmental control. The replacement of the hydroxyproline (Hyp) residues in a collagen peptide with carboxylate-modified Hyp residues gave a petide tha

CYCLIC PEPTIDES AS C5 A RECEPTOR ANTAGONISTS

The invention relates to cyclic peptide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to cyclic peptide C5a receptor antagonists of formula (Ia)or formula (Ib), or pharmaceutically acceptable salts thereof,wherein R1a, R1b, R2, R3 and R4 areas defined in the description. C5a receptor antagonists are potentially useful in the treatment of a wide range of 1 disorders,including inflammatory disorders and immune disorders.

Scaling the Amphiphilic Character and Antimicrobial Activity of Gramicidin S by Dihydroxylation or Ketal Formation

The acid lability of aliphatic ketals, which often serve as protection groups for 1,2-diols, is influenced by their local structural environment. The acetonide of the protected amino acid cis-dihydroxyproline (Dyp) is a typical protecting group cleavable by traces of TFA. The tricyclic acetonide of the dipeptide d-Hot-Tap is resistant to TFA and thus can serve as a bioorthogonal modification of bioactive peptides. With the aim of improving antimicrobial activity and hemolytic properties, we use these reactivity differences to scale the membrane affinity of the decapeptide Gramicidin S cyclo(d-Phe-Pro-Val-Orn-Leu-)2 (GS). The cis-dihydroxylated amino acids are used to increase the polarity of GS or obversely decrease the polarity by stereoselective ketal formation with an aliphatic ketone. While Dyp (GS mimetic 15) has only minimal influence on the biological properties of GS, d-Hot-Tap at the position of d-Phe1-Pro2 eradicates the biological activity (GS mimetic 16). The acid-stable ketals 17-19 are bioorthogonal modifications which reconstitute the biological activity of GS. We describe an improved synthesis of orthogonally protected Fmoc-Dyp-acetonide (9) and of several Fmoc-d-Hot-Tap-ketals for solid-phase peptide synthesis.