21193-75-9

Usage

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 21193-75-9 differently. You can refer to the following data:
1. D-Galactal is an important building block for both solution- and solid-phase synthesis of oligosaccharides.
2. Important building block for both solution- and solid-phase synthesis of oligosaccharides.

Purification Methods

Recrystallise D-galactal from EtOAc, EtOH or EtOAc/MeOH. [Overend et al. J Chem Soc 675 1950, Wood & Fletcher J Am Chem Soc 79 3234 1957, Distler & Jourdian J Biol Chem 248 6772 1973, Beilstein 17 III/IV 2332.]

InChI:InChI=1/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6-/m1/s1

Upstream product

• 2873-29-2 D-glucal triacetate 
• 4098-06-0 triacetyl-D-galactal 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 2914-23-0 barium methoxide 
• 144071-49-8 1,2,3,4,6-penta-O-acetyl-D-allopyranose 
• 53369-42-9 2,3,4,6-tetra-O-acetyl-α-D-allo-pyranosyl bromide 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 14125-64-5 (2R,3R)-3-hydroxy-2-(hydroxymethyl)-2H-pyran-4(3H)-one 
• 1075748-94-5 C₃₈H₄₆O₄Si₂ 
• 125948-55-2 1,5-anhydro-3,6-di-O-acetyl-2-deoxy-D-ribo-hex-1-enitol 

Downstream Products

• 138406-76-5 Acetic acid (2S,3R,4S,5R)-5-acetoxy-4-((2S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 136520-46-2 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol 
• 63914-24-9 1-O-acetyl-2,6-anhydro-5-deoxy-D-arabino-hex-5-enitol 
• 4098-06-0 triacetyl-D-galactal 
• 118396-86-4 3,6-Di-O-acetyl-D-galactal 
• 124579-81-3 1,5-Anhydro-2-deoxy-3-O-methyl-D-lyxo-hex-1-enitol 
• 16740-98-0 1,5-anhydro-3,4,6-tri-O-methyl-2-deoxy-D-lyxo-hex-1-enitol 
• 166021-01-8 1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol 
• 173008-15-6 1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enopyranose 
• 58394-32-4 1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose 
• 14086-08-9 (R)-2-(2-furyl)-1,2-ethanediol 
• 201053-37-4 (-)-3,6-O-bis(triisopropylsilyl)-D-galactal 
• 3971-45-7 methyl 2-deoxy-α-D-galactopyranoside 
• 149625-80-9 1,5-anhydro-6-O-triisopropylsilyl-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 

Relevant academic research and scientific papers

DIASTEREOSELECTIVE SYNTHESIS OF BRANCHED 2-DEOXY SUGARS VIA RADICAL C-C BOND FORMATION REACTIONS

From glycals 1 and 6, 2-deoxy sugars can be synthesized in 40-72percent yields.With 1,2-disubstituted alkenes 3 this radical C-C bond formation reaction leads with high stereoselectivity to the isomers 4 and 8.

2-nitroglycal and efficient synthesis method thereof

The invention discloses an efficient synthesis method of 2-nitroglycal, and belongs to the technical field of synthesis of sugar. The structure of the 2-nitroglycal is shown in the specification. Secondly, the invention also provides a preparation method of the 2-nitro saccharide alkene, and the preparation method provided by the invention can be used for efficiently preparing the 2-nitroglycal through one-step synthesis.

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides

The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.

Method for stereoselectively synthesizing beta-2-deoxyglycoside bond

The invention discloses a method for stereoselectively synthesizing a beta-2-deoxyglycoside bond. The method comprises the following steps: performing glycosylation on 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene serving as a donor, a saccharide receptor and a molecular sieve under the condition of the existence of an accelerant, wherein an isopropyl acetal protectivegroup is mounted on a 3-site hydroxyl and a 4-site hydroxyl of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene and a TBDPS is mounted on the 6-site of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene; through the synergistic effect of the protective groups, sugar ring conformation of the donor is controlled, and the stereoselective synthesis of a beta-configuration is realized. According to the method, the stereoselectivity of the glycosylation can be controlled effectively and stereoselectively; the method is wide in substrate application range and convenient to operate; raw materials are easy to obtain; side reactions of the glycosylation are few; a target product is high in yield and optical purity; a new design thought is provided for the research of the glycosylation.

Stereospecific C-Glycosylation by Mizoroki–Heck Reaction: A Powerful and Easy-to-Set-Up Synthetic Tool to Access α- and β-Aryl-C-Glycosides

A stereospecific Mizoroki–Heck cross-coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either α- or β-aryl-C-glycosides depending solely on the configuration at C3 was achieved. The reaction was easy to set up because no specific precautions were required concerning moisture or oxygen, and it proceeded by a chirality transfer from C3 to C1. After optimization of cross-coupling conditions, various prepared glycals (7 examples) and arenes (10 examples) were tested, leading stereospecifically to the corresponding aryl-C-glycosides with a carbonyl group at C3, thus opening up new horizons for the total synthesis of glycosylated natural products.

Synthesis of Altrose Poly-amido-saccharides with β-N-(1→2)- d -amide Linkages: A Right-Handed Helical Conformation Engineered in at the Monomer Level

The design and synthesis of amide-linked saccharide oligomers and polymers, which are predisposed to fold into specific ordered secondary structures, is of significant interest. Herein, right-handed helical poly amido-saccharides (PASs) with β-N-(1→2)-d-amide linkages are synthesized by the anionic ring-opening polymerization of an altrose β-lactam monomer (alt-lactam). The right-handed helical conformation is engineered into the polymers by preinstalling the β configuration of the lactam ring in the monomer via the stereospecific [2+2] cycloaddition of trichloroacetyl isocyanate with a d-glycal possessing a 3-benzyloxy group oriented to the α-face of the pyranose. The tert-butylacetyl chloride initiated polymerization of the alt-lactam proceeds smoothly to afford stereoregular polymers with narrow dispersities. Birch reduction of the benzylated polymers gives water-soluble altrose PASs (alt-PASs) in high yields without degradation of the polymer backbone. Circular dichroism analysis shows the alt-PASs adopt a right-handed helical conformation in aqueous solutions. This secondary conformation is stable over a wide range of different conditions, such as pH (2.0 to 12.0), temperature (5 to 75 °C), ionic salts (2.0 M LiCl, NaCl, and KCl), as well as in the presence of protein denaturants (4.0 M urea and guanidinium chloride). Cytotoxicity studies reveal that the alt-PASs are nontoxic to HEK, HeLa, and NIH3T3 cells. The results showcase the ability to direct solution conformation of polymers through monomer design. This approach is especially well-suited and straightforward for PASs as the helical conformations formed result from constraints imposed by the relatively rigid and sterically bulky repeating units.