20316-77-2

Basic information

• Product Name: (3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane
• Synonyms: (3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane
• CAS NO: 20316-77-2
• Molecular Formula: C₁₅H₂₄O₆
• Molecular Weight: 300.3475
• Mol File: 20316-77-2.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 355.2°Cat760mmHg
• Flash Point: 139.6°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 6.5E-05mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: (3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane(20316-77-2)
• EPA Substance Registry System: (3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane(20316-77-2)

Safety Data

• Hazardous Substances Data: 20316-77-2(Hazardous Substances Data)

Usage

General Description

The chemical compound "(3R,4S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7,7-dimethyl-4-prop-2-enoxy-2,6,8-trioxabicyclo[3.3.0]octane" is a complex organic compound with a bicyclic structure. It contains three oxygen atoms and is classified as a tricyclic ether. The compound also contains a prop-2-enoxy group and two methyl groups, giving it a total of seven carbon atoms. This chemical structure is important in organic chemistry and may have applications in pharmaceuticals, materials science, or other fields.

InChI:InChI=1/C15H24O6/c1-6-7-16-11-10(9-8-17-14(2,3)19-9)18-13-12(11)20-15(4,5)21-13/h6,9-13H,1,7-8H2,2-5H3/t9-,10-,11+,12?,13?/m1/s1

Upstream product

• 107-05-1 3-chloroprop-1-ene 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 109-64-8 1,3-dibromo-propane 
• 109-70-6 1.3-chlorobromopropane 
• 106-95-6 allyl bromide 
• 99605-27-3 3-O-(tert-butyldimethylsilyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 13964-22-2 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 753488-63-0 1,2:5,6-di-O-isopropylidene-3-O-methylprenyl-α-D-glucofuranose 
• 224317-43-5 1,2:5,6-di-O-isopropylidene-3-O-(3'-methyl-2'-butenyl)-α-D-glucofuranose 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 64656-76-4 Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose 

Downstream Products

• 524037-13-6 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 144685-52-9 ³O-(3-diphenylphosphinopropyl)-¹O,²O:⁵O,⁶O-diisopropylideneglucofuranose 
• 144685-48-3 Bis-{3-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-propyl}-phenyl-phosphane 
• 39698-00-5 acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 

Relevant articles and documents

Synthesis and characterization of a new methacrylic glycomonomer

The carbohydrate containing monomer 3-O-(2′-hydroxy-3′- methacryloyloxypropyl)-1,2: 5,6-di-O-isopropylidene-α-D-glucofuranose was easily prepared from D-glucose and methacrylic acid in 4 steps. The structure of the new methacrylic monomer was confirmed using FTIR, NMR (including 1H-NMR, 13C-NMR, COSY, HMQC and HMBC), and HPLC-MS. This work is part of our groups effort to obtain new polymers based on renewable resources with enhanced biodegradability and biocompatibility.

A ring-closing metathesis approach to a synthesis of the B ring of eleutherobin

A short and efficient RCM route is reported for the construction of the key nine-membered B ring of eleutherobin starting from the readily available 1,2,5,6-diisopropylidene-D-glucose.

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

An efficient, eco-compatible diversity-oriented synthesis (DOS) approach for the generation of library of sugar embedded macrocyclic compounds with various ring size containing 1,2,3-triazole has been developed. This concise strategy involves the iterative use of readily available sugar-derived alkyne/azide-alkene building blocks coupled through copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction followed by pairing of the linear cyclo-adduct using greener reaction conditions. The eco-compatibility, mild reaction conditions, greener solvents, easy purification and avoidance of hazards and toxic solvents are advantages of this protocol to access this important structural class. The diversity of the macrocycles synthesized (in total we have synthesized 13 macrocycles) using a set of standard reaction protocols demonstrate the potential of the new eco-compatible approach for the macrocyclic library generation.

Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo

Glycoconjugation is a promising strategy for specific targeting of cancer. In this study, we investigated the effect of d-glucose substitution position on the biological activity of glucose-platinum conjugates (Glc-Pts). We synthesized and characterized all possible positional isomers (C1α, C1β, C2, C3, C4, and C6) of a Glc-Pt. The synthetic routes presented here could, in principle, be extended to prepare glucose conjugates with different active ingredients, other than platinum. The biological activities of the compounds were evaluated both in vitro and in vivo. We discovered that varying the position of substitution of d-glucose alters not only the cellular uptake and cytotoxicity profile but also the GLUT1 specificity of resulting glycoconjugates, where GLUT1 is glucose transporter 1. The C1α- and C2-substituted Glc-Pts (1α and 2) accumulate in cancer cells most efficiently compared to the others, whereas the C3-Glc-Pt (3) is taken up least efficiently. Compounds 1α and 2 are more potent compared to 3 in DU145 cells. The α- and β-anomers of the C1-Glc-Pt also differ significantly in their cellular uptake and activity profiles. No significant differences in uptake of the Glc-Pts were observed in non-cancerous RWPE2 cells. The GLUT1 specificity of the Glc-Pts was evaluated by determining the cellular uptake in the absence and in the presence of the GLUT1 inhibitor cytochalasin B, and by comparing their anticancer activity in DU145 cells and a GLUT1 knockdown cell line. The results reveal that C2-substituted Glc-Pt 2 has the highest GLUT1-specific internalization, which also reflects the best cancer-targeting ability. In a syngeneic breast cancer mouse model overexpressing GLUT1, compound 2 showed antitumor efficacy and selective uptake in tumors with no observable toxicity. This study thus reveals the synthesis of all positional isomers of d-glucose substitution for platinum warheads with detailed glycotargeting characterization in cancer.

Synthesis and NMR elucidation of four novel 2-(trimethylsilyl)ethyl glycosides

Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a short and efficient route starting from d-glucose. Their structures were elucidated by applying high-resolution mass spectra, and one-dimensional and two-dimensional NMR techniques.