22331-21-1

Usage

Uses

Used in Organic Synthesis:
3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose is used as a building block in organic synthesis for creating more complex molecules. Its unique structure and reactivity allow chemists to construct a wide range of compounds with diverse applications.
Used in Chemical Reactions:
In the field of chemical reactions, 3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose is utilized as a key intermediate. Its functional groups facilitate various chemical transformations, enabling the synthesis of novel compounds with potential applications in pharmaceuticals, materials science, and other industries.
Used in Research and Development:
3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose is employed in research and development as a valuable tool for exploring new chemical reactions and understanding the underlying mechanisms. Its unique properties make it an attractive candidate for studying reaction kinetics, selectivity, and other fundamental aspects of chemical processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose is used as a starting material for the synthesis of bioactive compounds. Its structural features can be exploited to design and develop new drugs with improved therapeutic properties.
Used in Materials Science:
3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose is also utilized in materials science for the development of advanced materials with specific properties. Its reactivity and structural features can be harnessed to create materials with applications in areas such as nanotechnology, polymer science, and biomaterials.

Upstream product

• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 2595-05-3 Diacetone D-glucose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 4205-23-6 D-gulose 
• 65434-49-3 3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose 
• 77-76-9 2,2-dimethoxy-propane 
• 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 
• 286011-06-1 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 
• 35777-79-8 5,6-di-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 22331-19-7 3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 
• 50-99-7 D-glucose 

Downstream Products

• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 405116-11-2 (S)-Benzyloxy-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-acetaldehyde 
• 405116-12-3 (2R,4R,5R)-4-((R)-1-Benzyloxy-2-hydroxy-ethyl)-2-phenyl-[1,3]dioxan-5-ol 
• 402474-66-2 (S)-Benzyloxy-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde 
• 405116-13-4 Benzoic acid (R)-2-benzyloxy-2-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester 
• 405116-14-5 (R)-2-Benzyloxy-2-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-ethanol 
• 405116-01-0 (R)-4-Benzyloxy-2-diazo-4-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid ethyl ester 
• 405116-00-9 (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-butyric acid ethyl ester 
• 405115-99-3 (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-hydrazono-butyric acid ethyl ester 
• 405115-96-0 (R)-4-Benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-3-hydroxy-butyric acid ethyl ester 
• 405115-98-2 (Z)-(R)-2-Acetoxy-4-benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid ethyl ester 
• 405115-97-1 (R)-3-Acetoxy-4-benzyloxy-4-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-2-diazo-butyric acid ethyl ester 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 5531-09-9 3-O-benzyl-D-allopyranose 

Relevant academic research and scientific papers

6-Methylpurine derived sugar modified nucleosides: Synthesis and evaluation of their substrate activity with purine nucleoside phosphorylases

6-Methylpurine (MeP) is cytotoxic adenine analog that does not exhibit selectivity when administered systemically, and could be very useful in a gene therapy approach to cancer treatment involving Escherichia coli PNP. The prototype MeP releasing prodrug, 9-(β-d-ribofuranosyl)-6-methylpurine, MeP-dR has demonstrated good activity against tumors expressing E. coli PNP, but its antitumor activity is limited due to toxicity resulting from the generation of MeP from gut bacteria. Therefore, we have embarked on a medicinal chemistry program to identify non-toxic MeP prodrugs that could be used in conjunction with E. coli PNP. In this work, we report on the synthesis of 9-(6-deoxy-β-d-allofuranosyl)-6-methylpurine (3) and 9-(6-deoxy-5-C-methyl-β-d-ribo-hexofuranosyl)-6-methylpurine (4), and the evaluation of their substrate activity with several phosphorylases. The glycosyl donors; 1,2-di-O-acetyl-3,5-di-O-benzyl-α-d-allofuranose (10) and 1-O-acetyl-3-O-benzyl-2,5-di-O-benzoyl-6-deoxy-5-C-methyl-β-d-ribohexofuran-ose (15) were prepared from 1,2:5,6-di-O-isopropylidine-α-d-glucofuranose in 9 and 11 steps, respectively. Coupling of 10 and 15 with silylated 6-methylpurine under Vorbrüggen glycosylation conditions followed conventional deprotection of the hydroxyl groups furnished 5'-C-methylated-6-methylpurine nucleosides 3 and 4, respectively. Unlike 9-(6-deoxy-α-l-talo-furanosyl)-6-methylpurine, which showed good substrate activity with E. coli PNP mutant (M64V), the β-d-allo-furanosyl derivative 3 and the 5'-di-C-methyl derivative 4 were poor substrates for all tested glycosidic bond cleavage enzymes.

The use of free radical cyclization in the synthesis of compounds related to the mannostatins

A study of the potential use of 5-exo free radical cyclizations in the synthesis of carbocyclic compounds related to the mannostatins 1 and 2 is described. The dithioacetal 8 was prepared and the methyl oxime moiety utilised as an intramolecular radical t

NOVEL PROCESS FOR MAKING ALLOFURANOSE FROM GLUCOFURANOSE

The present invention relates to the manufacture of allofuranose from glucofuranose as defined in the description and in the claim. Allofuranos is an intermediate in the manufacture of oligonucleotides which can be used as a medicament.

FUCOSIDASE INHIBITORS

The present disclosure relates, in general, to compounds useful as inhibitors of fucosidase enzymes, and to methods and compositions for the treatment of tumors or cancers, such as liver disorders and liver tumors (e.g., hepatocellular carcinoma), with a compound as disclosed herein.

Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B12 Biosynthesis

Comparative genomics of the bacterial thiamin pyrimidine synthase (thiC) revealed a paralogue of thiC (bzaF) clustered with anaerobic vitamin B12 biosynthetic genes. Here we demonstrate that BzaF is a radical S-adenosylmethionine enzyme that catalyzes the remarkable conversion of aminoimidazole ribotide (AIR) to 5-hydroxybenzimidazole (5-HBI). We identify the origin of key product atoms and propose a reaction mechanism. These studies represent the first step in solving a long-standing problem in anaerobic vitamin B12 assembly and reveal an unanticipated intersection of thiamin and vitamin B12 biosynthesis.

Titanocene dihalides and ferrocenes bearing a pendant α-d- xylofuranos-5-yl or α-d-ribofuranos-5-yl moiety. synthesis, characterization, and cytotoxic activity

Titanocene dichlorides of general formula [(η5-C 5H5)(η5-C5H4R) TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α- d-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl- α-d-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C 5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C 5H5)TiCl3] or a 0.5 mol amount of [TiCl 4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5- C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R 1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu) 2SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)2] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(η5-C5H4R)2Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(η5- C5H4R)2Fe] (R = 5-deoxy-1,2-di-O- isopropylidene-α-d-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-d-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(η5-C5H4R1)(η5- C5H4R2)Fe] (R1 = Xylf and R 2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.

Synthesis of 2′-O,4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase

The synthesis of 2′-O,4′-C-methylene-bridged bicyclic guanine ribonucleosides bearing 2′-C-methyl or 5′-C-methyl modifications is described. Key to the successful installation of the methyl functionality in both cases was the use of a one-pot oxidation-Grignard procedure to avoid formation of the respective unreactive hydrates prior to alkylation. The 2′-C-methyl- and 5′-C-methyl-modified bicyclic guanosines were evaluated, along with the known uracil-, cytosine-, adenine-, guanine-LNA and guanine-ENA nucleosides, as potential antiviral agents and found to be inactive in the hepatitis C virus (HCV) cell-based replicon assay. Examination of the corresponding nucleoside triphosphates, however, against the purified HCV NS5B polymerase indicated that LNA-G and 2′-C-methyl-LNA-G are potent inhibitors of both 1b wild type and S282T mutant enzymes in vitro. Activity was further demonstrated for the LNA-G-triphosphate against HCV NS5B polymerase genotypes 1a, 2a, 3a and 4a. A phosphorylation by-pass prodrug strategy may be required to promote anti-HCV activity in the replicon assay.

N-Thiocarbonyl iminosugars: Synthesis and evaluation of castanospermine analogues bearing oxazole-2(3H)-thione moieties

A straightforward and efficient synthetic route to a new class of glycosidase inhibitors containing an oxazole-2(3H)-thione moiety has been devised. The approach involves the formation of α-hydroxy ketones, which, after condensation with thiocyanic acid, leads to the formation of the heterocycle. By exploiting the ability of the nitrogen atom of oxazoline-2-thione precursors to act as nucleophiles in intramolecular addition, castanospermine analogues could be readily prepared in good overall yields. Glycosidase inhibitory activity compared to oxazolidinethione analogues showed a strong influence of the double bond, for example with pseudoiminosugar 19, by suppressing α-glucosidase inhibition and introducing, to a moderate level, β-glucosidase inhibitory activity. Reactivities showed the propensity of oxazole-2(3H)-thiones - especially when fused on carbohydrate frames - to convert into 1,3-oxazolidine-2-thione aminals through nucleophilic addition to the double bond, leading to unexpected tricyclic structure 21. Oxazole-2(3H)-thione moieties have been anchored onto carbohydrates in a five-step sequence that allows access to castanospermine analogues. Copyright

The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?

The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.

Synthesis of fused cyclic systems containing medium-sized rings through tandem ROM-RCM of norbornene derivatives embedded in a carbohydrate template

A general approach for the synthesis of fused cyclic systems containing medium-sized rings (7-9) has been developed. The key steps involve a diastereoface-selective Diels-Alder reaction of the dienophiles 4a-d attached to a furanosugar with cyclopentadiene and ring opening (ROM)-ring closing metathesis (RCM) of the resulting norbornene derivatives 10a-d and 11a-d. Diels-Alder reaction of the dienophiles 4a-d with cyclopentadiene in the absence of a catalyst produced 10a-d as the major product arising through addition of the diene to the unhindered Si-face. The most interesting and new aspect of the Diels-Alder reaction of these dienophiles is the accessibility of the Re-face that was blocked by the alkenyl chains under Lewis acid catalysis producing the diastereoisomers 11a-d exclusively. The reversal of facial selectivity from an uncatalyzed reaction to a catalyzed one is unprecedented. The observed stereochemical dichotomy is attributed to rotation of the enone moiety along the o bond linking the sugar moiety during formation of the chelate 13. This makes the Re-face of the enone moiety in 4a-d unhindered. Diels-Alder reaction of the carbocyelic analogue 15 under Lewis acid catalysis produced a 1:1 mixture of the adducts 16 and 17 confirming the participation of sugar ring oxygen in chelate formation. Finally ROM-RCM of 10a-d and 11a-d with Grubbs' catalyst afforded the cis-syn-cis and cis-anti-cis bicyclo-annulated sugars 21a-d and 23a-d, respectively, containing 7-9 membered rings.