109100-88-1

Basic information

• Product Name: {4-[2-(benzyloxy)-2-oxoethyl]-5-oxo-1,3-dioxolan-4-yl}acetic acid
• CAS NO: 109100-88-1
• Molecular Formula: C₁₄H₁₄O₇
• Molecular Weight: 294.2568
• Mol File: 109100-88-1.mol

Chemical Properties

• Boiling Point: 499°C at 760 mmHg
• Flash Point: 189.3°C
• Density: 1.361g/cm³
• Vapor Pressure: 8.94E-11mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: {4-[2-(benzyloxy)-2-oxoethyl]-5-oxo-1,3-dioxolan-4-yl}acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: {4-[2-(benzyloxy)-2-oxoethyl]-5-oxo-1,3-dioxolan-4-yl}acetic acid(109100-88-1)
• EPA Substance Registry System: {4-[2-(benzyloxy)-2-oxoethyl]-5-oxo-1,3-dioxolan-4-yl}acetic acid(109100-88-1)

Safety Data

• Hazardous Substances Data: 109100-88-1(Hazardous Substances Data)

Upstream product

• 4767-12-8 4,4-(5-oxo-1,3-dioxolane)diacetic acid anhydride 
• 100-51-6 benzyl alcohol 
• 77-92-9 citric acid 
• 144-16-1 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid) 

Downstream Products

• 184834-44-4 1,2-dibenzyl hydrogen citrate 
• 225232-42-8 (S)-1,2-dibenzyl hydrogen citrate 
• 252010-77-8 (S)-2-[(S)-2-(N-tert-butoxycarbonylamino)propanamido]ethyl 2,3-dibenzyl citrate 
• 225232-36-0 (R)-2-[(S)-2-(N-tert-butoxycarbonylamino)propanamido]ethyl 2,3-dibenzyl citrate 
• 225232-45-1 (R)-1,2-dibenzyl hydrogen citrate 

Relevant articles and documents

The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase

We describe the synthesis of a variety of lipophilic isosteres of nucleoside triphosphates as potential anti-HIV agents. The citrate molecule proved to be a good mimic of triphosphate by modelling in terms of charge and spatial distribution. Several lipophile derivatives of citrate were conjugated to the precedented anti-HIV nucleoside d4T via ester and amide linkages. A novel synthesis of 5'-amino-d4T is included. Intramolecular rearrangement of several amide-linked isosteres are also reported, along with an alternative synthetic strategy to the desired amide-linked isosteres.

Isosteres of nucleoside triphosphates

This paper describes the design and synthesis of lipophilic isosteres of nucleoside triphosphates as potential inhibitors of HIV reverse transcriptase. The isosteric replacement of the triphosphate group is a modification of the citrate group.

Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

Total synthesis of the siderophore vibrioferrin

Total synthesis of vibrioferrin (1), a siderophore, was achieved via chiral dibenzyl citrate separated by optical resolution. It was elucidated that the configuration of the citrate moiety of vibrio-ferrin was R.