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
• Article Data: 7

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

Chemical Properties

Colourless Liquid

Uses

Methyl 2,3-O-Isopropylidene-5-O-benzyl-β-D-ribofuranoside (cas# 33019-63-5) is a compound useful in organic synthesis.

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

• 67-56-1 methanol 
• 50-69-1 D-ribose 
• 67-64-1 acetone 
• 136136-22-6 ((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate 
• 55904-12-6 ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 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 
• 100-44-7 benzyl chloride 

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 
• 79064-00-9 (2R,3R,4S)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol 
• 79063-93-7 (2R,3R,4R)-1-Benzyloxy-5-methoxy-hexane-2,3,4-triol 

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.

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