14347-83-2

Basic information

• Product Name: (R)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE
• Synonyms: (R)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE;L-alpha,beta-isopropylidene glycerol gamma-benzyl ether;1,3-Dioxolane, 2,2-dimethyl-4-(phenylmethoxy)methyl-, (4R)-;1-Benzyl-2,3-isopropylidene-sn-glycerol, L-α,β-Isopropylideneglycerol-γ-benzyl ether;1,3-Dioxolane, 2,2-dimethyl-4-(phenylmethoxy)methyl-;1-Benzyl-2,3-isopropylidene-sn-glycerol;L-α,β-Isopropylideneglycerol-γ-benzyl ether;(R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane
• CAS NO: 14347-83-2
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.28
• Product Categories: Chiral Building Blocks;Dioxanes & Dioxolanes;Dioxolanes;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry
• Mol File: 14347-83-2.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 79-80 °C0.05 mm Hg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.039 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: n20/D 1.496
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE(14347-83-2)
• EPA Substance Registry System: (R)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE(14347-83-2)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 14347-83-2(Hazardous Substances Data)

Usage

General Description

"(R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane is a chemical compound which falls under the category of organic compounds, particularly the class of organooxygen compounds. This specific chemical is often identified by its unique molecular structure which includes a dioxolane, a five-membered unsaturated ring consisting of one oxygen atom and two carbon atoms, and a benzyl group, derived from benzene. Like its fellow chemicals with a dioxolane ring, this substance is typically characterized by its synthesis from 1,3-diol with acetone under acidic conditions. However, further properties may differ according to the effects of its benzyl group and its chirality, indicated by the '(R)' in its name. The '(R)' notation signifies the arrangement of the compound’s atoms in space, known as its stereochemistry. The exact properties, uses, and toxicity of (R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane largely depend on the context of its use.

InChI:InChI=1/C13H18O3/c1-13(2)15-10-12(16-13)9-14-8-11-6-4-3-5-7-11/h3-7,12H,8-10H2,1-2H3/t12-/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 77-76-9 2,2-dimethoxy-propane 
• 100-79-8 2,3-O-isopropylidene glycerol 
• 10567-18-7 (+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-octadecanoate 
• 20620-19-3 (2,2-dimethyl-1,3-dioxolane-4-yl)methyl caproate 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 189633-88-3 (S)-1,2-O-isopropylidene glycerol hexanoate 
• 60456-21-5 methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 100-44-7 benzyl chloride 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 67-64-1 acetone 

Downstream Products

• 119879-74-2 (R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propan-2-ol 
• 201732-38-9 ((R)-3-Benzyloxy-2-chloromethoxy-propoxy)-tert-butyl-diphenyl-silane 
• 201732-39-0 (R)-1-{[2-O-t-butyldiphenylsilyl-1-(benzyloxymethyl)ethoxy]methyl}thymine 
• 201732-43-6 (R)-4-amino-1-{[2-O-t-butyldiphenylsilyl-1-(benzyloxymethyl)ethoxy]methyl}-5-methyl-2,6-[1H,3H]-pyrimidione 
• 120362-29-0 (2-Benzyloxy-1-hydroxymethyl-ethoxymethyl)-phosphonic acid diethyl ester 
• 120362-30-3 Methanesulfonic acid 3-benzyloxy-2-(diethoxy-phosphorylmethoxy)-propyl ester 
• 120362-27-8 1-Benzyloxy-3-[(4-methoxy-phenyl)-diphenyl-methoxy]-propan-2-ol 
• 120362-33-6 (S)-1-<3-(Benzyloxy)-2-<(diethylphosphonyl)methoxy>propyl>cytosine 
• 120362-34-7 [2-(4-Amino-pyrimidin-2-yloxy)-1-benzyloxymethyl-ethoxymethyl]-phosphonic acid diethyl ester 
• 120362-28-9 {1-Benzyloxymethyl-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethoxymethyl}-phosphonic acid diethyl ester 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 

Relevant articles and documents

The Chiral Target of Daptomycin Is the 2R,2′S Stereoisomer of Phosphatidylglycerol

Daptomycin (dap) is an important antibiotic that interacts with the bacterial membrane lipid phosphatidylglycerol (PG) in a calcium-dependent manner. The enantiomer of dap (ent-dap) was synthesized and was found to be 85-fold less active than dap against

Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors

Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of l-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure-activity relationship studies of more than 100 "glycol surrogate"derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1-and 2-acyl lysophospholipids.

Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin-lipid interactions

Phosphatidylglycerophosphate methyl ester (PGP-Me), a major constituent of the archaeal purple membrane, is essential for the proper proton-pump activity of bacteriorhodopsin (bR). We carried out the first synthesis of the bisphosphate head group of PGP-M