362-42-5

Basic information

• Product Name: 2',3'-O-isopropylidene cytidine
• Synonyms: 2',3'-O-isopropylidene cytidine;2',3'-isopropylidenecytidine;2',3'-O-(1-Methylethylidene)cytidine;β-D-2',3'-O-(isopropylidene)cytidine
• CAS NO: 362-42-5
• Molecular Formula: C₁₂H₁₇N₃O₅
• Molecular Weight: 283
• Mol File: 362-42-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 238-240℃ (methanol )
• Boiling Point: 465.7°C at 760 mmHg
• Flash Point: 235.5°C
• Appearance: /
• Density: 1.66±0.1 g/cm3 (20℃ 760 Torr)
• Vapor Pressure: 1.25E-10mmHg at 25°C
• Refractive Index: 1.691
• PKA: 14.14±0.10(Predicted)
• CAS DataBase Reference: 2',3'-O-isopropylidene cytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-O-isopropylidene cytidine(362-42-5)
• EPA Substance Registry System: 2',3'-O-isopropylidene cytidine(362-42-5)

Safety Data

• Hazardous Substances Data: 362-42-5(Hazardous Substances Data)

Usage

Uses

2'',3''-Isopropylidenecytidine is an intermediate in synthesizing 5-Hydroxymethylcytidine-13CD2 (H947092), an analogue of 5-Hydroxymethylcytidine (H947090) which is a product in DNA hydroxymethylation.

InChI:InChI=1/C12H17N3O5/c1-12(2)19-8-6(5-16)18-10(9(8)20-12)15-4-3-7(13)14-11(15)17/h3-4,6,8-10,16H,5H2,1-2H3,(H2,13,14,17)

Upstream product

• 74848-82-1 4-(Ethoxymethyl-amino)-1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidin-2-one 
• 65-46-3 CYTIDINE 
• 16667-80-4 2',3'-O-isopropylidene-N⁴-acetylcytidine 
• 104-15-4 toluene-4-sulfonic acid 
• 39946-94-6 4-N-benzoyl-2',3'-O-isopropylidenecytidine 
• 67-56-1 methanol 
• 77787-58-7 N⁴-benzoyl-2',3'-O-isopropylidene-O²,5'-cyclocytidine 
• 67-64-1 acetone 
• 115269-11-9 1,2,3-tri-O-acetyl-5-O-benzoyl-β-D-ribofuranose 
• 5517-60-2 methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 36468-53-8 β-D-ribofuranose 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 2346620-55-9 molnupiravir acetonide 

Relevant articles and documents

The first silicon(iv) phthalocyanine-nucleoside conjugates with high photodynamic activity

A series of novel silicon(iv) phthalocyanines conjugated axially with different nucleoside moieties (uridine, 5-methyluridine, cytidine, and 5-N-cytidine derivatives) have been synthesized and evaluated for their photodynamic activities. The uridine-containing compound 1 exhibits the highest photocytotoxicity against HepG2 human hepatocarcinoma cells with an IC 50 value as low as 6 nM, which can be attributed to its high cellular uptake and non-aggregated nature in the biological media. This compound shows high affinity toward the mitochondria of HepG2 cells and causes cell death mainly through apoptosis upon illumination. The result indicates that 1 is a highly promising photosensitizer for photodynamic therapy.

Reactions Between Ribonucleoside Derivatives and Formaldehyde in Ethanol Solution

2',3'-O-Isopropylidene-adenosine, -cytidine, and -guanosine, (2a), (3a), and (4a), respectively react with formaldehyde in ethanol solution to give the corresponding N-ethoxymethyl derivatives, (2b), (3b), and (4b), respectively in good yields.

Preparation method of monabiravir

The preparation method of monabiravir involves the field of medical technology. The method takes cytidine (1) as the starting material, after hydroxyl protection to obtain Compound 2; Compound 2 is obtained by isobutyryl chloride acylation to obtain a double-acylated intermediate 3, Compound 3 undergoes regional selective deacylation and hydroxylamineization tandem reaction to obtain Compound 4, and finally Compound 4 is deprotected, refined to obtain the finished monabiravir (5), the process route is as follows:

Conversion of: N- acyl amidines to amidoximes: A convenient synthetic approach to molnupiravir (EIDD-2801) from ribose

An efficient method is described for the preparation of molnupiravir (EIDD-2801) an antiviral agent via regioselective conversion of an N-acyl-nucleoside intermediate, generated through stereo and regioselective glycosylation of protected ribose and N4-acetyl cytosine, to an amidoxime. This method avoids use of expensive starting materials, enzymes, complex reagents, and cumbersome purification procedures.

An axial nucleoside asymmetric modified silicon phthalocyanine and its preparation method and application

The invention discloses axial nucleoside asymmetrically-modified silicon phthalocyanine and a preparation method and application thereof, belonging to the preparation field of a photodynamic medicine or a photosensitizer. The axial nucleoside asymmetrically-modified silicon phthalocyanine disclosed by the invention can be applied to photodynamic treatment, photodynamic diagnosis or photodynamic disinfection as a photosensitizer, has the structural characteristic of axial asymmetric substitution, and shows good amphipathicity and excellent photodynamic activity.