362600-15-5

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-(hydroxymethyl)-, 9H-fluoren-9-ylmethyl ester, (3R,4R)-
• CAS NO: 362600-15-5
• Molecular Formula: C20H21NO4
• Molecular Weight: 339.391
• Mol File: 362600-15-5.mol

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-(hydroxymethyl)-, 9H-fluoren-9-ylmethyl ester, (3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-(hydroxymethyl)-, 9H-fluoren-9-ylmethyl ester, (3R,4R)-(362600-15-5)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-(hydroxymethyl)-, 9H-fluoren-9-ylmethyl ester, (3R,4R)-(362600-15-5)

Safety Data

• Hazardous Substances Data: 362600-15-5(Hazardous Substances Data)

Upstream product

• 71336-69-1 (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 267421-93-2 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine 
• 871086-00-9 (3S,4R)-1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylic acid 
• 362600-14-4 N-Fmoc-(3R,4S)-4-[(1S)-1,2-dihydroxyethyl]pyrrolidin-3-ol 
• 395076-07-0 N-Fmoc-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol 

Downstream Products

• 502485-10-1 C₄₁H₃₉NO₆ 
• 267421-93-2 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine 

Relevant articles and documents

Profiling base excision repair glycosylases with synthesized transition state analogs

Two base excision repair glycosylase (BER) transition state (TS) mimics, (3R,4R)-1-benzyl (hydroxymethyl) pyrrolidin-3-ol (1NBn) and (3R,4R)- (hydroxymethyl) pyrrolidin-3-ol (1N), were synthesized using an improved method. Several BER glycosylases that repair oxidized DNA bases, bacterial formamidopyrimdine glycosylase (Fpg), human OG glycosylase (hOGG1) and human Nei-like glycosylase 1 (hNEIL1) exhibit exceptionally high affinity (K d～pM) with DNA duplexes containing the 1NBn and 1N nucleotide. Notably, comparison of the Kd values of both TS mimics relative to an abasic analog (THF) in duplex contexts paired opposite C or A suggest that these DNA repair enzymes use distinctly different mechanisms for damaged base recognition and catalysis despite having overlapping substrate specificities.

Synthesis of 1′-aza-C-nucleosides from (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol

Pyrimidine 1′-aza-C-nucleosides are synthesised by the fusion of 5-bromouracil, 5-bromocytosine and 5-bromoisocytosine with (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol in 40-41% yield. A homologue of 1′-aza-Ψ-uridine is obtained in a Mannich reaction in 65% yield by treatment of the azasugar, paraformaldehyde and uracil. N-Alkylation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol with 6-chloromethyluracil gives the 6-regioisomeric homologue. (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol is synthesised in 25% overall yield from diacetone-D-glucose via 3-C-(azidomethyl)-3-deoxy-D-allose which is subjected to an intramolecular reductive amino alkylation reaction to give (3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol followed by Fmoc protection, oxidative cleavage of the triol group with further reduction of the obtained aldehyde and subsequent deprotection of the nitrogen atom.

Synthesis of an aza analogue of 2-deoxy-D-ribofuranose and its homologues

Azasugars were obtained in one-pot reactions by catalytic reduction reactions of amino group precursors in aldosugars followed by intramolecular reductive amino alkylation reactions. (3R,4S)-4-[(1S)-1,2-Dihydroxyethyl]pyrrolidin-3-ol was obtained from D-xylose by two different strategies through 3-C-cyano-3-deoxy-D-ribo-pentofuranose or 3-C-azidomethyl-3-deoxy-D-ribo-pentofuranose in 6 and 16% overall yields, respectively. The oxidative cleavage of the diol group in the corresponding Fmoc-azasugar followed by deprotection afforded (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4S)-4-[(1S,2R)-1,2,3-Trihydroxypropyl]pyrrolidin-3-ol was synthesized from diacetone-D-glucose through 3-deoxy-3-C-nitromethyl-D-allose and the overall yield was 7%.