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

Description

Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside is a colorless liquid chemical compound derived from ribose, a naturally occurring sugar. It is characterized by its isopropylidene group at the 2,3-O positions, which provides unique chemical properties and reactivity. Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside is widely utilized in the synthesis of various fine chemicals and serves as an intermediate in the production of different chemical substances.

Uses

Used in Fine Chemicals Industry:
Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside is used as a key intermediate for the synthesis of various fine chemicals. Its unique chemical structure allows for the creation of a diverse range of products, including pharmaceuticals, agrochemicals, and specialty chemicals. Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside's reactivity and functional groups make it a valuable building block in the development of novel molecules with specific applications.
Used in Industrial Applications:
In the industrial sector, Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside is employed in the production of intermediates for a wide range of chemical products. Its versatility and compatibility with various synthetic routes make it an essential component in the manufacturing process. Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside's role as an intermediate enables the creation of a multitude of end products, contributing to the advancement of various industries.
Overall, Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside is a versatile and valuable compound in the fields of fine chemicals and industrial applications. Its unique chemical properties and reactivity make it an essential component in the synthesis of a wide range of products, from pharmaceuticals to specialty chemicals, and its role as an intermediate in industrial processes further highlights its importance in the chemical industry.

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

• 50-69-1 D-ribose 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 38838-05-0 1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside 
• 70337-22-3 2,3-O-isopropylidene-D-ribose diethyl dithioacetal 
• 50767-74-3 methyl (methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uronate 
• 33019-63-5 (2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran 
• 38838-06-1 methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside 
• 85558-05-0 2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-1,3-diphenyl-[1,3,2]diazaphospholidine 
• 67-56-1 methanol 
• 532-20-7 D-Ribose 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 1824-96-0 methyl ribofuranoside 
• 10257-32-6 D-ribose 

Downstream Products

• 54622-95-6 (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid 
• 98807-30-8 N⁴-Benzoyl-1-(2,3-O-isopropylidene-α-D-ribofuranosyl)-cytosine 
• 39946-94-6 4-N-benzoyl-2',3'-O-isopropylidenecytidine 
• 14131-76-1 2-(((4R,6R)-6-methoxy-2,2-dimethyltetrahydrofuro [3,4-d][1,3]dioxol-4-yl)methyl)isoindoline-1,3-dione 
• 33019-63-5 (2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran 
• 85558-05-0 2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-1,3-diphenyl-[1,3,2]diazaphospholidine 
• 76479-97-5 methyl 2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-β-D-ribofuranoside 
• 140186-56-7 methyl 2,3-O-isopropylidene-5-O-(3,5-di-O-benzoyl-2-deoxy-α-D-ribofuranosyl)-α-D-ribofuranoside 
• 140186-66-9 methyl (2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-(1→5)-2,3-O-isopropylidene-β-D-ribofuranoside 
• 118967-98-9 methyl 5-O-(5-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside 
• 118967-99-0 methyl 5-O-(5-O-benzoyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 38838-05-0 1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside 
• 38838-06-1 methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside 

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.

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.

A facile ultrasound-assisted synthesis of methyl 2,3-O-isopropylidene-β-D-ribofuranoside from D-ribose and its use to prepare new 1,2,3-triazole glycoconjugates

The conversion of D-ribose into its 2,3-O-isopropylidene derivative using ultrasonic irradiation is described. The ultrasound proved to be an excellent alternative as the energy source for the reaction. Different reaction times were investigated, and shorter reaction times and high yield were achieved without the need for purification of the acetonide. The compound was then applied as the starting material in the synthesis of 23 new glycoconjugates of 1,2,3-triazole that are tethered together in different ways. The synthesized compounds were characterized by FTIR, 1H NMR, 13C NMR, and HRMS techniques.