28528-94-1

Basic information

• Product Name: 1-O,2-O:3-O,5-O-Diisopropylidene-α-D-glucofuranose
• Synonyms: 1-O,2-O:3-O,5-O-Diisopropylidene-α-D-glucofuranose
• CAS NO: 28528-94-1
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.2836
• Mol File: 28528-94-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-O,2-O:3-O,5-O-Diisopropylidene-α-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O,2-O:3-O,5-O-Diisopropylidene-α-D-glucofuranose(28528-94-1)
• EPA Substance Registry System: 1-O,2-O:3-O,5-O-Diisopropylidene-α-D-glucofuranose(28528-94-1)

Safety Data

• Hazardous Substances Data: 28528-94-1(Hazardous Substances Data)

Upstream product

• 82529-83-7 (3aR,3bS,7R,7aR,8aR)-7-(4-Methoxy-benzyloxymethyl)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine 
• 38838-11-8 6-bromo-6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 85951-10-6 6-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 762-72-1 allyl-trimethyl-silane 
• 149356-18-3 6-O-tert-butyldimethylsilyl-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 20847-06-7 O⁶-(toluene-4-sulfonyl)-D-glucose 
• 930805-68-8 succinic acid 2-{[4-(2-chloro-4-nitro-phenylazo)-phenyl]-ethyl-amino}-ethyl ester 2,2,5,5-tetramethyl-tetrahydro-1,3,4,6,8-pentaoxa-cyclopenta[a]inden-7-ylmethyl ester 
• 188199-13-5 Dimethyl-[(2R,3S,6S)-6-(2-methyl-cyclohex-2-enyl)-2-((3aR,3bS,7R,7aR,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-ylmethoxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-(1,1,2-trimethyl-propyl)-silane 
• 118968-00-6 3-O-(5-O-benzoyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-1,2-5,6-di-O-isopropylidene-α-D-glucofuranose 
• 118968-01-7 6-O-(5-O-benzoyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-1,2-5,6-di-O-isopropylidene-α-D-glucofuranose 
• 34322-91-3 1,2:3,5-bis-O-(1-methylethylidene)-6-(p-tolylsulfonyl)-α-D-glucofuranose 
• 76491-06-0 6-O-benzoyl-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose 

Relevant articles and documents

Glucose transporter 1-mediated vascular translocation of nanomedicines enhances accumulation and efficacy in solid tumors

Nanomedicine modification with ligands directed to receptors on tumor blood vessels has the potential for selectively enhancing nanomedicine accumulation in malignant tissues by overcoming the vascular barrier of tumors. Nevertheless, the development of broadly applicable ligand approaches capable of promoting the transvascular transport of nanomedicines in a wide spectrum of tumors has been elusive so far. By considering the indispensable and persistent glycolytic fueling of tumors, we developed glucose-installed polymeric micelles loading cisplatin (Gluc-CDDP/m) targeting the glucose transporter 1 (GLUT1), which is overexpressed in most tumors and present on vascular endothelial cells, toward improving the delivery efficiency and therapeutic efficacy. The design of the glucose ligands on Gluc-CDDP/m was engineered to control the conjugation via the carbon 6 of the glucose moieties, as well as the ligand density on the poly (ethylene glycol) (PEG) shell of the micelles. The series of micelles was then studied in vitro and in vivo against GLUT1-high human squamous cell carcinoma of the head and neck OSC-19 cells and GLUT1-low human glioblastoma-astrocytoma U87MG cells. Our results showed that precisely tuning the micelles to have glucose ligands on 25% of their PEG chains increased the efficacy against the tumors by significantly enhancing the tumor accumulation, even in GLUT1-low U87MG tumors. The enhancement of the intratumoral levels of these micelles was hindered by concomitant administration of glucose, or the GLUT1 inhibitor STF-31, confirming a GLUT1/glucose-mediated increment of the accumulation. Intravital confocal laser scanning microscopy imaging of tumor tissues further demonstrated the rapid extravasation and penetration of Gluc-CDDP/m in OSC-19 tumors compared to non-targeted CDDP/m. These findings indicate GLUT1-targeting as a promising approach for overcoming the vascular barrier and boosting the delivery of nanomedicine in tumors.

Highly efficient rhodium catalysts for the asymmetric hydroformylation of vinyl and allyl ethers using C1-symmetrical diphosphite ligands

Here, we describe the successful application of novel glucofuranose-derived 1,3-diphosphites in the rhodium-catalysed asymmetric hydroformylation of vinyl acetate, 2,5-dihydrofuran and 2,3-dihydrofuran. In the hydroformylation of vinyl acetate, total regioselectivity and high ee (up to 73%) were obtained. When 2,3- and 2,5-dihydrofuran were the substrates, total chemo- and regioselectivities were achieved together with ees up to 88%. These results correspond to the highest ee values reported to date in the asymmetric hydroformylation of these substrates. The HP-NMR studies of the [RhH(CO) 2(L)] species (L=15 and 17) demonstrated that both ligands coordinate to the Rh centre in an eq-eq fashion. The complex [RhH(CO)2(15)] was detected as a single isomer with characteristic features of eq-eq coordination. However, the broadening of the corresponding signals indicated that this species is rapidly interchanging in solution. In contrast, complex [RhH(CO) 2(17)] was detected as a mixture of two conformational isomers at low temperature due to the greater flexibility of the monocyclic backbone of this ligand.

Naturalised dyes: A simple straightforward synthetic route to a new class of dyes - Glycoazodyes (GADs)

We report a process to naturalise synthetic azodyes through their linkage with lactose, or its monosaccharide components, either galactose or glucose, to enhance their solubility, as many other natural dyes. This modification allows the dyeing process of

Intramolecular hydrogen bonding (P=O-H) stabilizes the chair conformation of six-membered ring phosphates

Six-membered cyclic phosphates (2-phenoxy-2-oxo-1,3,2-dioxaphosphorinanes) bearing an internal protected or unprotected hydroxyl group were designed, synthesized, and studied by NMR and computational methods. Selective opening of O-isopropylidene-protecte

The mechanism of the hydroxyl → halogen exchange reaction in the presence of triphenylphosphine, N-bromosuccinimide, and N,N-dimethylformamide: Application of a new Vilsmeier-type reagent in carbohydrate chemistry

Triphenylphosphine reacts with N-bromosuccinimide to give a phosphonium salt (13), which reacts with N,N-dimethylformamide to afford N,N-dimethylsuccinimidomethaniminium bromide (16). The latter product reacts with an alcohol to give an O-formiminium compound 17, and, in the presence of an alcohol, 13 is transformed into an alkoxyphosphonium intermediate (14). Both 4 and 17 can be converted by heating into an alkyl bromide. Hydrolysis of 17 gives the corresponding O-formyl derivative. Reaction of 1.2:5.6-di-O-isopropylidene-α-D-glucofuranose with 13 or 16 gave 6-bromo-6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose and a possible mechanism for these reactions is suggested. An efficient method for the preparation of 3-deoxy-3-halogeno-1,2:5,6-di-O-isopropylidene-α-D-allofuranose derivatives and a new procedure for selective O-formylation are described.

ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL)AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS

The 4-methoxybenzyl (MPM) protecting group for hydroxy functions is readily removed with DDQ in dichloromethane containing a small amount of water at room temperature.Under these neutral conditions, several other protecting and functional groups remained unchanged. 3,4-Dimethoxybenzyl (DMPM groups are more reactive than MPM groups with DDQ.The benzyl (Bn) protecting group was removed by catalitic hydrogenation over Raney nickel.Selective deprotection of DMPM, MPM and Bn groups is also presented.

SPECIFIC REMOVAL OF O-METHOXYBENZYL PROTECTION BY DDQ OXIDATION

Methoxybenzyl protecting groups of alcohols were readily and efficiently removed with DDQ in CH2Cl2-H2O at room temperature.Under these neutral conditions, other usual protecting groups, isopropylidene, methoxymethyl, benzyloxymethyl, tetrahydropyranyl, acetyl, t-butyldimethylsilyl, benzyl, benzoyl, and tosyl, as well as functional groups, epoxide, double bond, and ketone, were remained unchanged.