13199-25-2

Basic information

• Product Name: 2,3-O-Isopropylidene-D-ribofuranoside
• Synonyms: 2,3-O-ISOPROPYLIDENE-D-RIBOFURANOSE;2,3-O-ISOPROPYLIDENE-ALPHA,BETA-D-RIBOFURANOSE;2,3-O-ISOPROPYLIDENE-ALPHA,SS-D-RIBOFURANOSE;2,3-O-ISOPROPYLIDENE-A,B-D-RIBOFURANOSE;2,3-O-Isopropylidene-D-ribofuranoside;2,3-O-Isopropylidene-D-ribose;2,3-O-Isopropylidene-ɑ,β-D-ribofuranose;2,3Isopropylidene-alpha,~-D-ribofuranose
• CAS NO: 13199-25-2
• Molecular Formula: C₈H₁₄O₅
• Molecular Weight: 190.19
• EINECS: -0
• Product Categories: 13C & 2H Sugars;aldehydes;Carbohydrates & Derivatives
• Mol File: 13199-25-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 337.426 °C at 760 mmHg
• Flash Point: 157.87 °C
• Appearance: Pale yellow oily liquid
• Density: 1.267 g/cm³
• Vapor Pressure: 7.17E-06mmHg at 25°C
• Refractive Index: 1.485
• Storage Temp.: 2-8°C
• Solubility: Soluble in acetone.
• PKA: 13.46±0.20(Predicted)
• CAS DataBase Reference: 2,3-O-Isopropylidene-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-Isopropylidene-D-ribofuranoside(13199-25-2)
• EPA Substance Registry System: 2,3-O-Isopropylidene-D-ribofuranoside(13199-25-2)

Safety Data

• Hazardous Substances Data: 13199-25-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oily Liquid

Uses

2,3-O-Isopropylidene-alpha,beta-D-ribofuranose is used as a pharmaceutical intermediate.

InChI:InChI=1/C8H14O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-7,9-10H,3H2,1-2H3

Upstream product

• 50-69-1 D-ribose 
• 67-64-1 acetone 

Downstream Products

• 96690-02-7 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 
• 141607-35-4 C₂₄H₃₂O₅Si 
• 681853-93-0 (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol 
• 68703-51-5 5'-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 89243-23-2 1',1'-bis<5-acetoxy-3-methyl-5-oxo-1-phenyl-Δ²-4-pyrazyl>-1'-deoxy-4',5'-di-O-acetyl-2',3'-O-isopropylidene-D-ribitol 
• 118349-35-2 5-amino-3-benzylthio-4-carbamoyl-1-(2',3'-O-isopropylidene-β-D-ribofuranosyl)pyrazole 
• 118349-38-5 5-amino-3-benzylthio-4-cyano-1-(2',3'-O-isopropylidene-β-D-ribofuranosyl)pyrazole 
• 118349-43-2 5-amino-4-carbamoyl-3-phenyl-1-(2',3'-O-isopropylidene-β-D-ribofuranosyl)pyrazole 
• 118349-45-4 5-amino-4-cyano-3-phenylyl-1-(2',3'-O-isopropylidene-β-D-ribofuranosyl)pyrazole 
• 254114-43-7 3-(5'-O-tert-Butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-8-hydrazino-6-(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine 
• 254114-42-6 3-(5'-O-tert-Butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-6,8-bis(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine 
• 254114-44-8 3-(5'-O-tert-Butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-6-(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine 
• 254114-37-9 Bromo-[(3aR,4R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid ethyl ester 

Relevant articles and documents

Thioimidate N-oxides: From nature to synthetic pathways

Inspired by the unexpected reactivity of desulfated naturally occurring glucoraphenin, methods to synthesize thioimidate N-oxides (TIO) have been devised on simple or carbohydrate templates. Either through halocyclization or under Mitsunobu conditions, the starting thiohydroximates cyclized to generate efficiently the corresponding TIO. Georg Thieme Verlag Stuttgart ? New York.

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Stereoselective total synthesis of goniothalesdiol A via chiron approach

The stereocontrolled synthesis of goniothalesdiol A, a dihydroxylated tetrahydropyran compound, has been accomplished using d-ribose as chiral precursor. The key steps involved are aryl Grignard reaction, stereoselective alkoxy-directed keto reduction, and intramolecular oxy-Michael addition.

Synthesis and l-fucosidase inhibitory activity of a new series of cyclic sugar imines-in situ formation and assay of their saturated counterparts

The synthesis of a series of aryl-substituted cyclic sugar imines was performed via a tandem nucleophilic addition/substitution reaction. The so-obtained ketimines displayed fucosidase inhibitory activities (IC50 = 46-556 μM). Their reduced counterparts were prepared and assayed after addition of sodium borohydride to the enzymatic assay stock solution. The pyrrolidines strongly inhibit fucosidase (IC50 = 0.65-150 μM).