35958-64-6

Usage

Uses

Used in Synthetic Chemistry:
3,5,6-Tri-O-benzyl-D-glucofuranose is used as a protecting group for the hydroxyl group in carbohydrate derivatives, facilitating the synthesis of complex carbohydrate structures.
Used in Pharmaceutical Industry:
3,5,6-Tri-O-benzyl-D-glucofuranose is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Natural Product Synthesis:
3,5,6-Tri-O-benzyl-D-glucofuranose is used as a versatile building block in the chemical synthesis of natural products, enabling the production of bioactive compounds with various biological properties.
Used in Carbohydrate Chemistry Research:
3,5,6-Tri-O-benzyl-D-glucofuranose is used as an important tool in carbohydrate chemistry research, aiding in the exploration of carbohydrate structures, reactivity, and potential applications in various fields.

Upstream product

• 53928-30-6 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside 
• 171072-99-4 3,4,6-tri-O-benzyl-1,2-O-sulfinyl-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 67-56-1 methanol 

Downstream Products

• 51515-91-4 1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose 
• 135284-41-2 3,5,6-Tris-O-benzyl-D-sorbitol 
• 110237-87-1 (2S,3R)-3-Benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-2,3-dihydro-furan 
• 58794-70-0 1,2-O-isopropylidene-3,4,5,6-tetra-O-benzyl-D-sorbitol 
• 58846-24-5 3,4,5,6-tetra-O-benzyl-D-sorbitol 
• 135284-42-3 (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol 
• 171072-99-4 3,4,6-tri-O-benzyl-1,2-O-sulfinyl-α-D-glucofuranose 
• 871508-18-8 1,4-anhydro-3,5,6-tri-O-benzyl-D-fructose 
• 903876-37-9 1,4-anhydro-3,5,6-tri-O-benzyl-D-tagatose 
• 903876-33-5 1,4-anhydro-3,5,6-tri-O-benzyl-D-glucitol 
• 903876-36-8 1,4-anhydro-3,5,6-tri-O-benzyl-D-galactitol 
• 871508-19-9 1,4-anhydro-3,5,6-tri-O-benzyl-D-fructose diethyl acetal 
• 903876-38-0 1,4-anhydro-3,5,6-tri-O-benzyl-D-tagatose diethyl acetal 
• 903876-34-6 3,5,6-tri-O-benzyl-1,2-O-isopropylidene-4-O-tosyl-D-glucitol 

Relevant academic research and scientific papers

INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF

Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the i

Synthesis, antiproliferative activity and SAR analysis of (?)-cleistenolide and analogues

A new, modified total synthesis of (?)-cleistenolide (1) and sixteen new analogues or derivatives was achieved starting from commercially available 1,2-O-isopropylidene-α-D-glucofuranose. The synthesis of 1 proceeds in six steps and 67% overall yield, usi

Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity

An efficient synthesis of 1,2-trans-N-glycosylated derivatives from phthalimide and nitrobenzimidazole via 1,2-O-sulfinyl monosaccharides has been established. Such SN2-type displacements at the anomeric center are stereospecific, giving a sing

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.

First synthesis of 4a-carba-β-d-galactofuranose

The synthesis of 4a-carba-β-d-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the C{double bond, long}C double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity.

Synthesis of 1,4-anhydro-d-fructose and 1,4-anhydro-d-tagatose

1,4-Anhydro-d-fructose and 1,4-anhydro-d-tagatose were prepared from 1,2-O-isopropylidene-d-glucofuranose via the common intermediate 3,5,6-tri-O-benzyl-d-glucitol. The title compounds may be interesting anti-oxidants and feature activities akin to their natural pyranoid counterpart, 1,5-anhydro-d-fructose.

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).

A facile synthesis of 1,2-anhydroglycofuranose benzyl ethers

The synthesis of 1,2-anhydromanno-, -lyxo-, -gluco-, and -xylofuranose benzyl ethers was successfully achieved via intramolecular S(N)2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonate

ACID-CATALYZED CONVERSION OF 2-O-(2-HYDROXYPROPYL)-D-GLUCOSE DERIVATIVES INTO 1,2-O-(1-METHYL-1,2-ETHANEDIYL)-D-GLUCOSE ACETALS. STUDIES RELATED TO O-(2-HYDROXYPROPYL)CELLULOSE

The acid-catalyzed solvolysis of methyl 3,5,6-tri-O-benzyl-2-O-(2-hydroxypropyl)-α-D-glucofuranoside (1) in chloroform involves a neighboring-group attack on C-1 by the hydroxypropyl substituent, and opening of the furanoside ring to yield a diastereomeric pair of 3,5,6-tri-O-benzyl-1-Omethyl-1,2-O-(1-methyl-ethanediyl)-D-glucose acetals (2 and 3).The latter, which differ in configuration at C-8,represent a resolution of the enantiomeric forms of the original 2-O-(2-hydroxypropyl) group.In a succeeding reaction, the 1-methoxyl group of each acetal undergoes an intramolecular displacement by O-4, leading to the formation of the corresponding biycyclic acetals, i.e., the two diastereomers (4 and 5) of 3,5,6-tri-O-benzyl-1,2-O-(1-methyl-1,2-ethanediyl)-α-D-glucofuranose.Solvolysis of 6, the β anomer of 1, proceeds in an analogous manner, although more rapidly, to yield a corresponding pair of acyclic-aldose acetals (7 and 8), as well as bicyclic acetals 4 and 5.Similar results are observed for solvolysis in the 2-O-(2-hydroxyethyl) series, whereas the reaction of the 2-O-(2,3-epoxypropyl) counterpart of 1 (or 6) with hydrogen chloride affords the corresponding chloromethyl analogs of 4 and 5.In all of these series, one of each diastereomeric pair of products is more stable than the other, and reasons for this are considered.Evidence based on n.m.r.-spectral data and steric factors is presented to show that the configuration of the chiral center C-8 of 2, 4, and 7 is (S), whereas it is (R) in 3, 5, and 8.Also, conformational characteristics of the various solvolysis products are assessed, and mechanisms possibly involved in their formation are discussed.

1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose

The title compound 13 is prepared on different routes from suitable benzyl derivatives with gluco-configuration.Preparations use the susceptibility of axial 5-O-benzyl groups in this compounds to selective hydrogenolysis, thus allowing subsequent inversion of configuration in this position from D-gluco to L-ido by an oxidation/reduction sequence.Only 0.08percent of 13 are found in the equilibrium mixture of idose in acidic medium.It is shown with 4-C-methyltalose as example, that the amount of 1,6-anhydrofuranoses in these equilibria rises significantly by changing the hydroxy groups in 4-position from secondary to tertiary ones.