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

Downstream Products

• 77871-03-5 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-arabinofuranosyl)-L-hydroxyproline 
• 77871-03-5 2-N-(benzyloxycarbonyl)-4-O-(2,3,5-tri-O-benzyl-α-L-arabinofuranosyl)-L-hydroxyproline benzyl ester 
• 77871-03-5 2-N-(benzyloxycarbonyl)-4-O-(2,3,5-tri-O-benzyl-β-L-arabinofuranosyl)-L-hydroxyproline benzyl ester 
• 77884-93-6 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-L-arabinopyranosyl)-L-hydroxyproline 
• 77884-93-6 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-arabinopyranosyl)-L-hydroxyproline 
• 132592-10-0 (2S,4R)-4-(formyloxy)-1,2-pyrrolidinecarboxylic acid 1,2-bis(phenylmethyl ester) 
• 132592-06-4 (2S,4S)-4-(formyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 132592-11-1 (2S,4R)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 146900-33-6 (2S,4R)-4-(Benzyloxy-diisopropylamino-phosphanyloxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 132592-09-7 (2S,4R)-4-acetoxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 132591-96-9 (2S,4S)-4-acetoxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 132592-12-2 (2S,4R)-4-methoxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester) 
• 80134-55-0 N^α-Z-O²-(tetra-O-acetyl-β-D-glucopyranosyl)-Hyp-OBzl 

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

Structural development of cell-penetrating peptides containing cationic proline derivatives

We designed and synthesized a series of cell-penetrating peptides containing cationic proline derivatives (ProGu) that exhibited responsive changes in their secondary structures to the cellular environment. Effects of the peptide length and steric arrangement of the side chain in cationic proline derivatives [Pro4SGu and Pro4RGu] on their secondary structures and cell membrane permeability were investigated. Moreover, peptides 3 and 8 exhibited efficient intracellular delivery of plasmid DNA.

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.