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

• 38838-05-0 1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside 
• 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 
• 77-76-9 2,2-dimethoxy-propane 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 67-64-1 acetone 
• 67-56-1 methanol 
• 10257-32-6 D-ribose 
• 36468-53-8 β-D-ribofuranose 
• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 
• 50-69-1 D-ribose 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 1824-96-0 methyl ribofuranoside 

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.

Structure-property relationships of ribose based ionic liquids

The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.

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.