37077-81-9

Basic information

• Product Name: 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose
• Synonyms: alpha-D-ribofuranose, 1,2-O-(1-methylethylidene)-
• CAS NO: 37077-81-9
• Molecular Formula: C₈H₁₄O₅
• Molecular Weight: 190.1938
• Mol File: 37077-81-9.mol
• Article Data: 31

Chemical Properties

• Melting Point: 85 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• Boiling Point: 333°C at 760 mmHg
• Flash Point: 155.2°C
• Density: 1.267g/cm³
• Vapor Pressure: 1E-05mmHg at 25°C
• Refractive Index: 1.485
• PKA: 13.23±0.60(Predicted)
• CAS DataBase Reference: 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose(37077-81-9)
• EPA Substance Registry System: 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose(37077-81-9)

Safety Data

• Hazardous Substances Data: 37077-81-9(Hazardous Substances Data)

Usage

General Description

1,2-O-(1-methylethylidene)-alpha-D-ribofuranose is a chemical compound with the molecular formula C7H12O5. It is a derivative of ribose, a naturally occurring sugar. 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose is often used in organic chemistry and pharmaceutical research as a building block for the synthesis of various drugs and other bioactive molecules. Its structure includes a ribofuranose ring with an isopropylidene substituent at the 1 and 2 positions, which gives it unique chemical properties and reactivity. The compound is also known by the names isopropylidene ribose or isomaltol. Overall, 1,2-O-(1-methylethylidene)-alpha-D-ribofuranose is a versatile and important chemical for the development of various pharmaceutical and organic chemistry applications.

Upstream product

• 6698-46-0 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 190970-10-6 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose 
• 6612-91-5 ((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 532-20-7 D-xylofuranose 
• 37077-82-0 ((3aR,5R,6R,6aR)-6-acetoxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methyl acetate 
• 1187322-25-3 1,2-O-isopropylidene-5-acetyl-α-D-ribofuranose 
• 85951-12-8 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 
• 196868-07-2 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside 
• 80244-95-7 3,5-di-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 532-20-7 D-Ribose 
• 80244-96-8 5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose 

Downstream Products

• 20590-57-2 1,2-O-isopropylidene-5-O-trityl-α-D-ribofuranose 
• 16054-77-6 (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol 
• 1322748-56-0 N-benzyl-1,2-O-isopropylidene-3,5-dideoxy-3,5-imino-α-D-xylofuranose 
• 1322748-58-2 N-benzyl-1,3-dideoxy-1,3-imino-L-xylitol 
• 1338054-42-4 N-(p-methoxybenzyl)-1,3-dideoxy-1,3-imino-L-xylitol 
• 1338054-35-5 N-(p-methoxybenzyl)-1,2-O-isopropylidene-3,5-dideoxy-3,5-imino-α-D-xylofuranose 
• 561055-45-6 (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol 
• 213313-43-0 methyl 3,5-di-O-benzyl-D-arabinofuranoside 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 817204-28-7 C₂₀H₂₂O₅ 
• 35522-90-8 (3aR,5S,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid 

Relevant articles and documents

Reaction of acetylated carbohydrates with trimethylaluminum: concise synthesis of 1,2-O-isopropylidene d-ribofuranose

Treatment of β-d-ribose tetraacetate with trimethylaluminum gives α-3,5-O-acetyl-1,2-O-isopropylidene-d-ribofuranoside in excellent yield. This reaction allows for efficient and high-yielding installation of the 1,2-isopropylidene acetal (acetonide), whic

Development of 2-Deoxy-2-[18F]fluororibose for Positron Emission Tomography Imaging Liver Function in Vivo

Life-threatening acute liver failure can be triggered by a variety of factors, including common drugs such as acetaminophen. Positron emission tomography (PET) is rarely used to monitor liver function, in part because of a lack of specific imaging agents for liver function. Here we report a new PET probe, 2-deoxy-2-[18F]fluororibose ([18F]-2-DFR), for use in imaging liver function. [18F]-2-DFR was synthesized and validated as a competitive substrate for the ribose salvage pathway. [18F]-2-DFR was prepared through an efficient late stage radiofluorination. The desired selectivity of fluorination was achieved using an unorthodox protecting group on the precursor, which could withstand harsh SN2 reaction conditions with no side reactions. [18F]-2-DFR accumulated preferentially in the liver and was metabolized by the same enzymes as ribose. [18F]-2-DFR could distinguish between healthy liver and liver damaged by acetaminophen. [18F]-2-DFR is expected to be a useful PET probe for imaging and quantifying liver functions in vivo, with likely significant clinical utility.

NOVEL SPIROBICYCLIC INTERMEDIATES

The present invention relates to novel spirobicyclic intermediates useful in the synthesis of spirobicyclic nucleoside analogues.

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.