4099-85-8

Basic information

• Product Name: Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside
• Synonyms: METHYL 2,3-O-ISOPROPYLIDEN-D-RIBOFURANOSE;METHYL-2,3-O-ISOPROPYLIDENE-ALPHA,BETA-D-RIBOFURANOSIDE;METHYL 2,3-O-ISOPROPYLIDENE-B-D-RIBOFURANOSIDE;METHYL 2,3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSIDE;EINECS 223-865-8;METHYL 2,3-O-ISOPROPYLIDENE-SS-D-RIBOFURANOSIDE;2,3-O-Isopropylidene-B-D-ribofuranoside;((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
• CAS NO: 4099-85-8
• Molecular Formula: C₉H₁₆O₅
• Molecular Weight: 204.22
• EINECS: 223-865-8
• Product Categories: Carbohydrates & Derivatives
• Mol File: 4099-85-8.mol
• Article Data: 125

Chemical Properties

• Boiling Point: 75°C/0.3mm
• Flash Point: 127.529 °C
• Appearance: Clear Yellow/Oil
• Density: 1.233 g/cm³
• Vapor Pressure: 0.000282mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Refrigerator
• Solubility: Soluble in chloroform, dichloromethane, ethanol, ethyl acetate,
• PKA: 14.14±0.10(Predicted)
• CAS DataBase Reference: Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside(4099-85-8)
• EPA Substance Registry System: Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside(4099-85-8)

Safety Data

• Hazardous Substances Data: 4099-85-8(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Liquid

Uses

Methyl 2,3-O-isopropylidene-beta-D-ribofuranoside is used for the manufacture of fine chemicals, and Industrial use resulting in manufacture of intermediates.

InChI:InChI=1/C9H16O5/c1-9(2)13-6-5(4-10)12-8(11-3)7(6)14-9/h5-8,10H,4H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 532-20-7 D-Ribose 
• 67-64-1 acetone 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 67814-68-0 2,3-O-isopropylidene-β-D-ribofuranose 
• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 50-69-1 D-ribose 
• 77-76-9 2,2-dimethoxy-propane 
• 36468-53-8 β-D-ribofuranose 
• 1236149-23-7 methyl 5-O-(tetrahydro-2H-pyran-2-yl)-(2,3-O-methylethylidene)-β-D-ribofuranoside 
• 1236149-25-9 methyl 5-O-(tetrahydrofuran-2-yl)-(2,3-O-methylethylidene)-β-D-ribofuranoside 
• 1824-96-0 methyl ribofuranoside 
• 70209-11-9 methyl (1R,2R,3R,4R)-2,3-O-isopropylidene-5-O-trifluoromethanesulfonyl-beta-D-ribofuranoside 

Downstream Products

• 98807-30-8 N⁴-Benzoyl-1-(2,3-O-isopropylidene-α-D-ribofuranosyl)-cytosine 
• 39946-94-6 4-N-benzoyl-2',3'-O-isopropylidenecytidine 
• 459426-88-1 (4R,5R)-5-((S)-2-Benzyloxy-1-hydroxy-2-methyl-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 459426-89-2 (S)-2-Benzyloxy-1-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol 
• 459426-96-1 2-Benzyloxy-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-one 
• 459426-91-6 (4S,5S)-4-((S)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane 
• 459426-98-3 (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane 
• 459426-90-5 (S)-2-Benzyloxy-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol 
• 459426-97-2 (R)-2-Benzyloxy-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 69260-71-5 doxifluridine 
• 144732-43-4 (3aR,6R,6aR)-4-Methoxy-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxole 

Relevant articles and documents

Some intramolecular rearrangements when pentofuranoses are treated with diethylaminosulphur trifluoride (DAST)

Treatment of methyl 2,3-O-isopropylidene-β-D-ribofuranoside with DAST gave a good yield of 2,3-O-isopropylidene-5-O-methyl-β-D-ribofuranosyl fluoride in which the methoxy group had migrated from C-1 -> C-5 and been replaced with retention of configuration by fluorine.The corresponding aldehyde when treated under similar conditions underwent a similar migration to give 5-deoxy-5-fluoro-2,3-O-isopropylidene-5-O-methyl-β-D-ribofuranosyl fluoride.A similar migration occurred with methyl 2',3'-di-O-acetyl-β-D-ribofuranoside and with acetyl 2,3-O-isopropylidene-D-ribofuranose but not with 1,2,3-tri-O-acetyl-D-ribofuranose.Thus the migration depends upon the migratory aptitude of the substituent at C-1 and the conformation of the furanose ring.Two ribofuranosyl fluorides were used as starting materials from which to make nucleosides by the method of Noyori and Hayoshi.

Selective cleavage of 2,3-O-isopropylidene group: A case of anchimeric assistance from O-glycoside

Alkyl 2,3-O-isopropylidene-5-O-methoxymethylfuranoside derivatives undergo selective cleavage of the 2,3-O-isopropylidene group, if oriented cis to the O-glycoside, in the presence of trifluoroacetic acid. Otherwise, the cleavage of the 5-O-methoxymethyl group is favoured over the 2,3-O-isopropylidene group.

The reaction of O-isopropylidene pentodialdo-1,4-furanoses with lithium diisopropylamide

Three O-isopropylidene group-protected pentose aldehydes (methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside (1), methyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside (2), and 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (3)) were treated at -30°C with lithium diisopropylamide (LDA) and the mixtures obtained were reduced with LiAlH4. The products, obtained in moderate yields, proved that deacetonation occurred followed by aldol reactions between aldehydes 1-3 and acetone. Copyright (C) 1999 Elsevier Science Ltd.

The quaternization reaction of 5-o-sulfonates of methyl 2,3-o-isopropylidene-β-D-ribofuranoside with selected heterocyclic and aliphatic amines

The synthesis of N-((methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside)-5-yl) ammoniumsalts are presented. To determine the effect of the nucleophile type and outgoing group on the quaternization reaction, selected aliphatic and heterocyclic aromatic amines reacted with: methyl 2,3-O-isopropylidene-5-O-tosyl-β-D-ribofuranoside or methyl 2,3-O-isopropylidene-5-O-mesyl-β-D -ribofuranoside ormethyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranosidewere performed on amicro scale. High-resolution 1H- and 13C-NMRspectraldata for all newcompoundswere recorded. Additionally, the single-crystalX-raydiffraction analysis formethyl 2,3-O-isopropylidene-5-O-mesyl-β-D-ribofuranoside and selected in silico interaction models are reported.

Sugar vanadates: Synthesis and characterisation of mannopyranoside and ribofuranoside esters incorporating VO3+

The sugars, methyl 4,6-di-O-methyl-α-D-mannopyranoside (H2m) and methyl 5-O-methyl-β-D-ribofuranoside (H2r) have been synthesized. These react smoothly with [VIVO(L)(H2O)] in methanol in air affording the dark coloured vanadates [VvO(Hm)(L)] and [VvO(Hr)(L)] in excellent yields (L2- = N-salicylideneglycinate). The crystal structure determination of [VvO(Hm)(L)] revealed five-membered chelation of VO3+ by the alcoholic and alkoxide oxygen atoms of the monoionised carbohydrate. The two atoms lie respectively trans to the oxo oxygen and aldimine nitrogen atoms. The five V-O bonds are unequal and span the range 1.57-2.37 A. The asymmetric unit of the complex consists of two metrically similar molecules locked in carboxylate-alcohol O ... O hydrogen bonding generating a macrocyclic cavity. In solution each ester displays a single 51V resonance near δ -544. The 1H NMR parameters of the alkoxidic and alcoholic CH protons and of OMe protons are consistent with the O,O-chelation mode for both the vanadates.

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.

MEAYAMYCIN ANALOGUES AND METHODS OF USE

Compounds according to formula (I), where R is as defined herein, have anti-cancer properties.

BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION

The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.