753497-92-6

Basic information

• Product Name: [5(R)-(4(R)-fluorobenzyloxymethyl)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-methanol
• CAS NO: 753497-92-6
• Molecular Weight: 270.301
• Mol File: 753497-92-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [5(R)-(4(R)-fluorobenzyloxymethyl)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [5(R)-(4(R)-fluorobenzyloxymethyl)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-methanol(753497-92-6)
• EPA Substance Registry System: [5(R)-(4(R)-fluorobenzyloxymethyl)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-methanol(753497-92-6)

Safety Data

• Hazardous Substances Data: 753497-92-6(Hazardous Substances Data)

Upstream product

• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 459-46-1 4-Fluorobenzyl bromide 

Downstream Products

• 753497-94-8 5(S)-((4R)-fluoro-benzyloxymethyl)-2,2-dimethyl-[1,3]-dioxolane-4(S)-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis and biological evaluation of new cross-conjugated dienone marine prostanoid analogues

The synthesis of a series of brominated cross-conjugated dienones, marine prostanoid analogues, was considered using two cyclopentannelation processes, from enamine (by a domino 3-aza Claisen/Mannich reaction) and from dioxolane ester alkylation followed by intramolecular Wittig reaction. All the compounds synthesized featured the same cross-conjugated dienone system, with a vicinal syn or anti diol on the ω-chain. The replacement of the ω-side-chain of the natural prostanoids with a 1-hydroxyphenyl-butyl moiety gave new prostanoids (32-34) with good cytotoxicities. In a second series of products, the possibility of a shorter α-side-chain bearing a simple phenyl ester was investigated. The results indicated a dramatic increase in the cytotoxicity (39, 40, 43, 44). Finally, in a third series, the ω- 1-hydroxyphenyl-butyl was replaced by a 1-hydroxymethyloxybenzyl chain. These simpler compounds (45,46,47,48, 60) are still highly cytotoxic, in the medium range of 60 nM, close to the value of natural punaglandins.