33019-63-5

Basic information

• Product Name: Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside
• Synonyms: Methyl2,3-O-isopropylidene-5-O-benzyl-β-D-ribofuranoside;Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside;(3aR,4R,6R,6aR)-4-(benzyloxymethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole;Methyl 2,3-O-(1-Methylethylidene)-5-O-(phenylMethyl)-β-D-ribofuranoside;Methyl 5-O-Benzyl-2,3-O-isopropylidene-β-D-ribofuranoside
• CAS NO: 33019-63-5
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.34
• Product Categories: Carbohydrates & Derivatives
• Mol File: 33019-63-5.mol

Chemical Properties

• Boiling Point: 147-149°C/0.3mm
• Flash Point: 155.489 °C
• Appearance: colourless liquid
• Density: 1.176 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside(33019-63-5)
• EPA Substance Registry System: Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside(33019-63-5)

Safety Data

• Hazardous Substances Data: 33019-63-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside is used as a synthetic intermediate for the creation of various complex organic molecules. Its unique structure allows it to be a versatile building block in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside is used as a key component in the development of novel drug candidates. Its ability to be modified and incorporated into complex molecular structures makes it a valuable asset in the design and synthesis of new therapeutic agents.
Used in Agrochemical Industry:
Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside is also employed in the agrochemical industry for the synthesis of bioactive compounds with potential applications in pest control, crop protection, and other agricultural settings. Its versatility in organic synthesis enables the development of innovative products that can address various challenges in agriculture.
Used in Specialty Chemicals:
In the specialty chemicals sector, Methyl 2,3-O-isopropylidene-5-O-benzyl-beta-D-ribofuranoside is utilized for the production of unique and high-value chemicals that serve specific purposes in various industries. These can include applications in materials science, coatings, adhesives, and other industrial processes that require specialized chemical inputs.

InChI:InChI=1/C16H22O5/c1-16(2)20-13-12(19-15(17-3)14(13)21-16)10-18-9-11-7-5-4-6-8-11/h4-8,12-15H,9-10H2,1-3H3/t12-,13-,14-,15-/m1/s1

Upstream product

• 23276-32-6 benzyl 2,3-O-isopropylidene-D-ribofuranoside 
• 100-44-7 benzyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 55904-12-6 ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 136136-22-6 ((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate 
• 29325-28-8 (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 
• 1256911-57-5 (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H-pyran-2-yl)oxy-4-hexenal 
• 1256911-56-4 (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H-pyran-2-yl)oxy-4-hexenol 
• 1256911-55-3 (E,4R,5S)-6-(tert-butyldimethylsilyl)oxy-4,5-isopropylidenedioxy-1-(tetrahydropyran-2-yl)oxy-2-hexene 
• 1256911-54-2 (E)-3-((4R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 
• 179237-62-8 (2S,3S)-2,3-O-isopropylidene-2,3,4-trihydroxybutanal tert-butyldimethylsilyl ether 
• 1256911-53-1 ((4R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 1256911-52-0 (2R,3S)-4-(tert-butyldimethylsilyl)oxy-2,3-isopropylidenedioxybutyl acetate 
• 532-20-7 D-Ribose 

Downstream Products

• 532-20-7 D-Ribose 
• 124151-36-6 5-O-benzyl-1,2,3-tri-O-acetyl-D-ribofuranoside 
• 118964-46-8 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol 
• 118964-44-6 2,5-di-O-benzyl-β-D-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol 
• 118964-47-9 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-D-ribitol 
• 118964-42-4 5-O-Allyl-1-O-(3-O-allyl-2,5-di-O-benzyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol 
• 118964-41-3 1-O-(2-O-Acetyl-3-O-allyl-5-O-benzyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol 
• 118964-52-6 (2R,3R,4S,5R)-4-Allyloxy-2-((2S,3R,4R)-5-allyloxy-2,3,4-tris-benzyloxy-pentyloxy)-5-benzyloxymethyl-tetrahydro-furan-3-ol 
• 118964-43-5 1-O-(2,5-Di-O-benzyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol 
• 118964-38-8 Acetic acid (2R,3R,4R)-4-acetoxy-2-benzyloxymethyl-5-chloro-tetrahydro-furan-3-yl ester 
• 124151-37-7 Acetic acid (3R,4R,5R)-4-allyloxy-5-benzyloxymethyl-2-chloro-tetrahydro-furan-3-yl ester 
• 118964-40-2 (3aR,5R,6R,6aR)-6-Allyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 118964-42-4 (2R,3R,4R,5R)-3-Allyloxy-5-((S)-5-allyloxy-2,3,4-tris-benzyloxy-pentyloxy)-4-benzyloxy-2-benzyloxymethyl-tetrahydro-furan 
• 118964-41-3 Acetic acid (2R,3R,4R,5R)-4-allyloxy-2-((S)-5-allyloxy-2,3,4-tris-benzyloxy-pentyloxy)-5-benzyloxymethyl-tetrahydro-furan-3-yl ester 

Relevant articles and documents

Alkoxyl Migration in Displacement of a 5-Trifluoromethanesulfonyloxy Group from Ribofuranosides

Methyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranoside (2) reacts at room temperature with primary aralkanols such as benzyl alcohol and the steroid alcohols 3a,b in dichloromethane and in the presence of sodium sulfate to give the corresponding aralkyl 2,3-O-isopropylidene-5-O-methyl-β-D-ribofuranosides 5a,b and 11 in 40-45percent yields.Migration of the methoxyl group from C-1 to C-5, via a tricyclic oxonium ion (7a), is suggested as the basis of formation of the new β-glycoside.Anchimeric assistance by a benzyloxy group in the displacement of the sulfonate is observed in the reaction of benzyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranoside (14) with methanol, which affords methyl 5-O-benzyl-2,3-O-isopropylidene-β-D-ribofuranoside (15) in 40percent yield on treatment with Na2SO4 in CH2Cl2.The elements of anomeric control in these facile transformations remain to be elaborated.

A novel pentose synthesis via palladium(II)-catalyzed cyclization of an unstable hemiacetal

PdCl2(PhCN)2 (5 mol%)-catalyzed cyclization of a hemiacetal derived from (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H- pyran-2-yl)-4-hexenal and methanol gave substituted furanoside in moderate yield, exclusively via 5-exo-mode cyclization, without the need for a reoxidant. New stereogenic centers at C1 and C4 on the tetrahydrofuran ring showed preferential 1R and 4R stereochemistry due to anomeric effect (n oσ*c-o) and A1,2 strain, respectively. This methodology was applied to stereocontrolled synthesis of pentoses: D-ribose and L-lyxose. The Japan Institute of Heterocyclic Chemistry.

Adhesin-oligosaccharide conjugate vaccine for Haemophilus influenzae

Disclosed herein are immunogenic polysaccharide-H. influenzae adhesin protein conjugates, a purified H. influenzae adhesin protein and related proteins and polypeptides, DNA useful for producing the proteins, synthetic polyribosylribotol phosphate (PRP) o

Synthesis of methyl 2-O-allyl-(and 3-O-allyl-)5-O-benzyl-β-D-ribofuranoside

D-Ribose was converted into methyl 5-O-benzyl-β-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (which was also synthesised from 3-O-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose) into the known 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose. Methyl 3-O-allyl-5-O-benzyl-β-D-ribofuranoside was converted into methyl 2-O-allyl-5-O-benzyl-β-D-ribofuranoside via methyl 2-O-allyl-5-O-benzyl-3-O(prop-1-enyl)-β-D-ribofuranoside.

A NEW APPROACH TO THE SYNTHESIS OF A DIMERIC FRAGMENT OF THE CAPSULAR POLYSACCHARIDE OF HAEMOPHILUS INFLUENZAE type b

The synthesis of the monomeric fragment of the Haemophilus influenzae type b (HIb) polysaccharide starting from orthoacetate 7 is described.The construction of the dimer is also reported.

HIGHLY STEREOSELECTIVE C-α-D-RIBOFURANOSYLATION. REACTIONS OF D-RIBOFURANOSYL FLUORIDE DERIVATIVES WITH ENOL TRIMETHYLSILYL ETHERS AND ALLYLTRIMETHYLSILANE

2,3,5-Tri-O-methyl-D-ribofuranosyl fluoride (6), 2,3-di-O-benzyl-5-O-methyl-D-ribofuranosyl fluoride (7), and 5-O-benzyl-2,3-di-O-methyl-D-ribo-furanosyl fluoride (8) were obtained in 57 (6α, 15; and 6β, 42), 87 (7α, 22; and 7β, 65) and 85.5 (8α, 35.5; an