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

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

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 
• 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 
• 67-56-1 methanol 
• 532-20-7 D-Ribose 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 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 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 1000609-88-0 ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate 

Downstream Products

• 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 
• 81823-38-3 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-D-erythro-pentos-4-ulose dimethyl acetal 
• 211110-96-2 Benzoic acid (R)-ethoxycarbonyl-((3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl ester 
• 67737-49-9 methyl 5-O-benzyl-α-D-ribofuranoside 
• 67737-48-8 methyl 5-benzyloxy-β-D-ribofuranoside 
• 69603-05-0 methyl-(O⁵-benzyl-O²,O³-carbonyl-β-D-ribofuranoside) 
• 115130-28-4 2,3-di-O-benzyl-5-O-methyl-β-D-ribofuranosyl fluoride 

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.

Increasing the H+ exchange capacity of porous titanium phosphonate materials by protecting defective P-OH groups

Hierarchically macro-/mesoporous titanium phosphonates with enlarged H + exchange capacity were synthesized in the presence of a series of alkyl amines that acted as protective groups for the defective P-OH, which were used as promising solid acid catalysts to replace conventional liquid acid catalysts and acidic resins in some acid-catalytic reactions.

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.

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.

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.