191480-69-0

Usage

Uses

Used in Pharmaceutical Industry:
(1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene is used as a building block in organic synthesis for the preparation of various pharmaceuticals and natural products. Its structural features and functional groups make it a versatile intermediate in the production of complex organic molecules, which can be further modified or combined to create new drugs with specific therapeutic effects.
Used in Organic Synthesis:
In the field of organic synthesis, (1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene is used as a key intermediate for the synthesis of complex organic molecules. Its unique structure allows for a wide range of chemical reactions, enabling the creation of diverse compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 542-92-7 cyclopenta-1,3-diene 
• 3587-60-8 Benzyloxymethyl chloride 
• 100-39-0 benzyl bromide 
• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 850224-36-1 (1S,2R)-2-(hydroxymethyl)cyclopent-3-enol 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 

Downstream Products

• 325480-46-4 (1R,2S,3S,4S)-4-benzyloxy-3-benzyloxymethylcyclopentane-1,2-diol 
• 325480-47-5 (1S,2R,3S,4S)-4-benzyloxy-3-benzyloxymethylcyclopentane-1,2-diol 
• 114826-94-7 (1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol 
• 114884-15-0 1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 648414-58-8 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)thymine 
• 911366-21-7 C₂₂H₂₆O₄ 
• 1020110-10-4 (3S,4R)-3-(benzyloxy)-4-(benzyloxymethyl)cyclopentanone 
• 1416986-51-0 C₂₄H₃₁NO₃S 
• 1416986-52-1 C₃₀H₃₇NO₃S 
• 1416986-57-6 C₃₀H₃₇NO₃S 
• 1416986-53-2 [(1S,2R)-1-benzyloxy-2-benzyloxymethyl-4-phenylcyclopent-4-yl]amine 
• 1416986-54-3 C₃₂H₃₆N₂O₅ 
• 1416986-55-4 C₃₁H₃₂N₂O₄ 
• 1416986-56-5 C₁₇H₂₀N₂O₄ 

Relevant academic research and scientific papers

Preparation method of oxa-dicyclohexane compound

The invention provides a preparation method of an entecavir intermediate, and particularly relates to a preparation method of an oxabicyclo [3.1.0] hexane compound (NT02). According to the preparation method, hydrogen peroxide is adopted as an oxygen source to replace tert-butyl hydroperoxide, the cost is low, the method is simple, the product yield is remarkably improved, and the preparation method is very suitable for industrial production and application.

Preparation method of entecavir intermediate

The invention provides a preparation method of an entecavir intermediate, and particularly relates to a preparation method of (1S-(1[alpha], 2[alpha], 3[beta], 5[alpha])-2-((benzyloxy) methyl)-6-oxabicyclo [3.1. 0] hexyl-3-alcohol and an oxabicyclo compound (NT02). The invention provides a brand new preparation route and reaction process conditions, and has the advantages of high operation safety, simple method, low cost and high yield. The product yield is obviously improved, and the method is very suitable for industrial production and application.

METTL3 MODULATORS

Provided are compounds of Formula (I') or (II'), or pharmaceutically acceptable salts thereof, and methods for their use and production.

PCSK9 INHIBITORS AND METHODS OF USE THEREOF

The invention relates to a novel inhibitor pharmacophore of PCSK9 and heteroaryl compounds that bind the PCSK9 protein.

PCSK9 INHIBITORS AND METHODS OF USE THEREOF

The invention relates to novel heteroaryl compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cardiovascular diseases, and methods treating sepsis or septic shock, using the novel heterocyclic compounds disclosed herein.

Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-d-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads

2-Deoxy-α-d-ribose-1-phosphate is of great interest as it is involved in the biosynthesis and/or catabolic degradation of several nucleoside analogues of biological and therapeutic relevance. However due to the lack of a stabilising group at its 2-position, it is difficult to synthesize stable prodrugs of this compound. In order to overcome this lack of stability, the synthesis of carbasugar analogues of 2-deoxyribose-1-phosphate was envisioned. Herein the preparation of a series of prodrugs of two carbocyclic analogues of 2-deoxyribose-1-phosphate using the phosphoramidate ProTide technology, along with their biological evaluation against HIV and cancer cell proliferation, is reported.

The synthesis of possible transition state analogue inhibitors of thymidine phosphorylase

The synthetically challenging SN2 transition state mimic for thymidine phosphorylase, along with its phosphonate analogue, were synthesised via a modified Corey-Link reaction in good overall yields and ensuring the correct stereochemical outcome.

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

Properties of oligonucleotide with phenyl-substituted carbocyclic nucleoside analogs for the formation of duplex and triplex DNA

(1S,3S,4R)-1-Phenyl-1-thymidyl-3-hydroxy-4-hydroxymethylcyclopentane (10) and their analogs were synthesized, incorporated into the oligodeoxynucleotides, and their properties were evaluated for the formation of duplex and triplex DNA. The known chiral cyclopentanone derivative was converted into the corresponding ketimine sulfonamide derivative, which was subjected to a stereoselective PhLi addition. The formed sulfonamide was hydrolyzed to afford the primary amino group, on which the thymine moiety was built. The benzyl protecting groups were removed to form the nucleoside analog having a phenyl group and the thymine unit at the 1 position of a carbocyclic skeleton (10). In the estimation of the oligodeoxynucleotides incorporating 10 for duplex and triplex formation, the carbocyclic nucleoside analog 10 did not show the stabilizing effect for duplex formation; on the other hand, it stabilized the triplex. Therefore, the skeleton of the phenyl-substituted carbocyclic nucleoside analog 10 may be a platform for the formation of stable triplex DNA.

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.