13039-67-3

Basic information

• Product Name: (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol
• Synonyms: (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol
• CAS NO: 13039-67-3
• Molecular Weight: 164.158
• Mol File: 13039-67-3.mol
• Article Data: 82

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol(13039-67-3)
• EPA Substance Registry System: (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol(13039-67-3)

Safety Data

• Hazardous Substances Data: 13039-67-3(Hazardous Substances Data)

Usage

General Description

The chemical compound (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol is a complex molecule with a molecular formula of C6H12O5. It consists of a five-membered ring with a hydroxymethyl group and a methoxy group attached to it, along with two hydroxyl groups at positions 3 and 4. (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol is a derivative of oxolane, a type of organic compound with a cyclic structure. The presence of hydroxyl and methoxy groups in this molecule suggests that it may have potential biological activities, and is commonly used in various pharmaceutical and chemical applications. Additionally, it is of interest to researchers in the fields of organic chemistry and biochemistry due to its unique structure and potential properties.

Upstream product

• 67-56-1 methanol 
• 1114-34-7 D-lyxose 
• 532-20-7 D-lyxose 
• 87-72-9 D-lyxose 
• 50-69-1 D-ribose 
• 532-20-7 D-Ribose 
• 189129-08-6 C₃₀H₂₆N₄O₈ 
• 850252-47-0 (4S,1'R)-4-(1'-hydroxy-2',2'-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-one 
• 1417423-72-3 C₁₃H₂₄O₆ 
• 875903-74-5 (4R,5R)-4-((R)-1-hydroxy-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-ol 
• 1417423-79-0 C₁₃H₂₆O₆ 
• 75-36-5 acetyl chloride 
• 10257-32-6 D-ribose 
• 2280-44-6 D-Glucose 

Downstream Products

• 2296-41-5 methyl-tri-O-methyl-arabinofuranoside 
• 86042-33-3 methyl 2,3,5-tri-O-p-toluyl-D-ribofuranoside 
• 108008-65-7 methyl 2,3,5-tri-O-(4-chlorobenzyl)-β-D-ribofuranoside 
• 59279-37-7 methyl 2,3,5-tri-O-(p-nitrobenzoyl)-β-D-ribofuranoside 
• 112245-59-7 methyl 3,5-O-isopropylidene-αβ-D-xylofuranoside 
• 83376-69-6 methyl 2,3-di-O-methyl-D-riboside 
• 83376-70-9 methyl 2,5-di-O-methyl-D-riboside 
• 83376-68-5 methyl 3,5-di-O-methyl-D-riboside 
• 2296-41-5 methyl 2,3,5-tri-O-methyl-D-ribofuranoside 
• 58763-00-1 ((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 532401-38-0 methyl 6-O-trityl-α,β-ribofuranoside 
• 67737-49-9 methyl 5-O-benzyl-α-D-ribofuranoside 

Relevant articles and documents

Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst

Transformation of sugars, while maintaining the intrinsic stereochemical structure, is desirable. However, such a transformation requires multistep synthesis with protection and deprotection of the OH groups. Herein, a new method for selective transformation of sugar derivatives into chiral building blocks and a diol synthon, with retention of the intrinsic configuration (stereo- and regioselectively), is demonstrated. The method is based on the selective recognition of cis-vicinal OH groups in sugars and leads to the one-pot removal of the cis-vicinal OH groups, without protection of OH groups (except the OH group of the hemiacetal group), over a heterogeneous CeO2-supported ReOx and Pd (ReOx-Pd/CeO2) catalyst by using H2 as a reducing agent.

Stereoselective Synthesis of Ribofuranoid exo-Glycals by One-Pot Julia Olefination Using Ribofuranosyl Sulfones

One-pot Julia olefination using ribofuranosyl sulfones is described. The α-anomers of the ribofuranosyl sulfones were synthesized with complete α-selectivity via the glycosylation of heteroarylthiols using ribofuranosyl iodides as glycosyl donors and the subsequent oxidation of the resulting heteroaryl 1-thioribofuranosides with magnesium monoperphthalate (MMPP). The Julia olefination of the α-ribofuranosyl sulfones with aldehydes proceeded smoothly in one pot to afford the thermodynamically less stable (E)-exo-glycals with modest-to-excellent stereoselectivity (up to E/Z = 94:6) under the optimized conditions. The E selectivity was especially high for aromatic aldehydes. In contrast, the (Z)-exo-glycal was obtained as the main product with low stereoselectivity when the corresponding β-ribofuranosyl sulfone was used (E/Z = 41:59). The remarkable impact of the anomeric configuration of the ribofuranosyl sulfones on the stereoselectivity of the Julia olefination has been rationalized using density functional theory (DFT) calculations. The protected ribose moiety of the resulting exo-glycals induced completely α-selective cyclopropanation on the exocyclic carbon-carbon double bond via the Simmons-Smith-Furukawa reaction. The 2-cyanoethyl group was found to be useful for the protection of the exo-glycals, as it could be removed without affecting the exocyclic C=C bond.

BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION

The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.