1146288-86-9

Upstream product

• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 542-92-7 cyclopenta-1,3-diene 
• 3587-60-8 Benzyloxymethyl chloride 

Downstream Products

• 1146288-87-0 (1R,2S,4S)-2-(benzyloxymethyl)-4-hydroxycyclopentyl methanesulfonate 
• 1146288-96-1 5'-O-benzyl-L-carba-ribothymidine 
• 1290137-21-1 (1S,3S)-3-(benzyloxymethyl)cyclopentanol 
• 1146288-94-9 (1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol 
• 1146288-90-5 (1R,4R)-4-(benzyloxymethyl)cyclopent-2-enyl benzoate 
• 1146288-93-8 (1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentyl benzoate 
• 1290137-27-7 (1R,2S,4R,5R)-4-(benzyloxymethyl)bicyclo[3.1.0]hexan-2-ol 
• 1290137-28-8 C₁₉H₂₂N₂O₃ 
• 1290137-29-9 (1R,2R,4R,5R)-4-(benzyloxymethyl)bicyclo[3.1.0]hexan-2-ol 
• 934986-74-0 (1R,4R)-4-(benzyloxymethyl)cyclopent-2-enol 
• 1353764-99-4 (1R,2R,3R,5S)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate 
• 1353764-98-3 (1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate 
• 1353742-20-7 (1R,2R,3R,4R)-4-(benzyloxy)-2-((benzyloxy)methyl)-3-hydroxycyclopentyl methanesulfonate 
• 1353742-21-8 (1R,2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-cyclopentyl methanesulfonate 

Relevant academic research and scientific papers

N-O bond as a glycosidic-bond surrogate: Synthetic studies toward polyhydroxylated N-alkoxypiperidines

A series of novel polyhydroxylated N-alkoxypiperidines has been synthesized by ring-closing double reductive amination (DRA) of highly functionalized 1,5-dialdehydes with various hydroxylamines. The required saccharide-based dialdehydes were prepared efficiently from sodium cyclopentadienylide in seven steps. A two-step protocol has been developed for the DRA; it led, after deprotection, to isofagomine, 3-deoxyisofagomine, and numerous other N-alkoxy analogues. The barrier to inversion in these polyhydroxylated N-alkoxypiperidine derivatives was found by variable-temperature NMR methods to be approximately 15 kcal mol-1. With the exception of N-hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond β-glucosidase. Copyright

Asymmetric synthesis of polyhydroxylated N -alkoxypiperidines by ring-closing double reductive amination: Facile preparation of isofagomine and analogues

A de novo synthesis of novel polyhydroxylated N-alkoxypiperidines based on the ring-closing double reductive amination of 1,5-dialdehydes, obtained by oxidative cleavage of cyclopentene derivatives, with O-substituted hydroxylamines is reported. Isofagomine was accessed by cleavage of the N-O bond of an N-alkoxypiperidine.

Synthesis of 2′,3′-modified carbocyclic L -nucleoside analogues

New divergent approaches to 2′,3′-modified carbocyclic L-nucleoside analogues starting from enantiomerically pure (1R,2S)- or (1S,2R)-2-(benzyloxymethyl)cyclopent-3-enol are described. In the key step, stereochemically pure cyclopentanols were condensed with N3-protected thymine through a modified Mitsunobu protocol. Moreover, several routes to different cyclopentanol derivatives, to prepare carbocyclic L-2′,3′-didehydro- 2′,3′-dideoxynucleosides (L-d4N), L-2′,3′- dideoxynucleosides (L-ddN), and L-ribonucleosides are reported. Copyright