114861-14-2

Basic information

• Product Name: 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose
• Synonyms: 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose;a-D-Xylofuranose, 5-O-[(1,1-diMethylethyl)diphenylsilyl]-1,2-O-(1-Methylethylidene)-;5-O-(tert-Butyldiphenylsilyl)-1,2-O-isopropylidene-alpha-D-xylofuranose;5-O-[(1,1-dimethylethyl)diphenylsilyl]-1,2-O-isopropylidene-±-D-xylofuranose;1,2-Di-O-isopropylidene-5-O-(t-butyldiphenylsilyl)--D-xylofuranose;(3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol(WX191815);5-O-(t-Butyldiphenylsilyl)-1,2-O-isopropylidene-a-D-xylofuranose
• CAS NO: 114861-14-2
• Molecular Formula: C₂₄H₃₂O₅Si
• Molecular Weight: 428.59338
• Mol File: 114861-14-2.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 495.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• PKA: 13.17±0.60(Predicted)
• CAS DataBase Reference: 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose(114861-14-2)
• EPA Substance Registry System: 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose(114861-14-2)

Safety Data

• Hazardous Substances Data: 114861-14-2(Hazardous Substances Data)

Usage

Molecular Structure

1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose consists of a xylofuranose ring with an isopropylidene group at the 1 and 2 positions, and a t-butyldiphenylsilyl group at the 5 position.

Complexity

This compound is highly complex due to its multiple functional groups and the arrangement of atoms within its structure.

Classification

It belongs to the group of xylofuranose derivatives and is a sugar derivative.

Functional Groups

The compound contains an isopropylidene group and a t-butyldiphenylsilyl group.

Usage

It is often used as a protecting group in the synthesis of other organic molecules, particularly in the field of carbohydrate chemistry.

Importance in Chemical Synthesis

The intricate structure and functionality of 1,2-O-Isopropylidene-5-O-(t-butyldiphenylsilyl)-alpha-D-xylofuranose make it a valuable tool for creating diverse and complex organic compounds.

Upstream product

• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 20590-53-8 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose 
• 58-86-6 D-xylose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 87-72-9 D-Xylose 
• 532-20-7 D-xylofuranose 
• 2460-44-8 β-D-xylopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 

Downstream Products

• 114861-15-3 5-O-<(1,1-dimethylethyl)diphenylsilyl>-1,2-O-(1-methylethylidene)-α-D-xylofuranose 3-(O-phenylthiocarbonate) 
• 114861-16-4 Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 75783-45-8 (3aR,5R,6aS)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-one 
• 213963-74-7 ((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane 
• 1101107-70-3 3-bromo-3-deoxy-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-α-D-ribofuranose 
• 130469-49-7 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose 
• 130469-50-0 6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine 

Relevant articles and documents

Exploring the purine core of 3′-C-ethynyladenosine (EAdo) in search of novel nucleoside therapeutics

A series of new nucleoside analogues based on a C-3 branched ethynyl sugar derivative as present in 3′-C-ethynylcytidine (ECyd) and -adenosine (EAdo), combined with modified purine bases was synthetized and evaluated against a broad array of viruses and t

PRMT5 INHIBITORS

The present invention provides a compound of formula (I) Formula (I) and the pharmaceutically acceptable salts, esters, and prodrugs thereof, are PRMT5 inhibitors. Also provided are methods of making compounds of formula (I), pharmaceutical compositions comprising compounds of formula (I), and methods of using these compounds to treat cancer, sickle cell, and hereditary persistence of foetal hemoglobin (HPFH) mutations.

Synthesis of Terminal Ribose Analogues of Adenosine 5′-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2

TRPM2 (transient receptor potential cation channel, subfamily M, member 2) is a nonselective cation channel involved in the response to oxidative stress and in inflammation. Its role in autoimmune and neurodegenerative diseases makes it an attractive pharmacological target. Binding of the nucleotide adenosine 5′-diphosphate ribose (ADPR) to the cytosolic NUDT9 homology (NUDT9H) domain activates the channel. A detailed understanding of how ADPR interacts with the TRPM2 ligand binding domain is lacking, hampering the rational design of modulators, but the terminal ribose of ADPR is known to be essential for activation. To study its role in more detail, we designed synthetic routes to novel analogues of ADPR and 2′-deoxy-ADPR that were modified only by removal of a single hydroxyl group from the terminal ribose. The ADPR analogues were obtained by coupling nucleoside phosphorimidazolides to deoxysugar phosphates. The corresponding C2″-based analogues proved to be unstable. The C1″- and C3″-ADPR analogues were evaluated electrophysiologically by patch-clamp in TRPM2-expressing HEK293 cells. In addition, a compound with all hydroxyl groups of the terminal ribose blocked as its 1″-β-O-methyl-2″,3″-O-isopropylidene derivative was evaluated. Removal of either C1″ or C3″ hydroxyl groups from ADPR resulted in loss of agonist activity. Both these modifications and blocking all three hydroxyl groups resulted in TRPM2 antagonists. Our results demonstrate the critical role of these hydroxyl groups in channel activation.