53008-61-0

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide
• CAS NO: 53008-61-0
• Molecular Weight: 650.553
• Mol File: 53008-61-0.mol

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide(53008-61-0)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide(53008-61-0)

Safety Data

• Hazardous Substances Data: 53008-61-0(Hazardous Substances Data)

Upstream product

• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate 
• 3866-62-4 2,3,4,6-tetrakis-O-(phenylmethyl)-1-O-acetyl-α-D-galactopyranose 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 

Downstream Products

• 112344-80-6 2-propenyl 2,3,4,6-tetra-O-benzyl-α-D-glactopyranoside 
• 4291-68-3 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 
• 64694-26-4 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 138902-22-4 3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 138511-92-9 1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-lyxo-hex-1-enitol 
• 853055-33-1 (2S,3R,4E)-2-azido-3-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-4-octadecene 
• 1085304-11-5 2-cyanoethyl-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N,N'-diisopropylphosphoramidite 
• 1217298-74-2 C₆₆H₈₃N₃O₈ 
• 1217298-93-5 C₅₉H₇₅N₃O₇ 
• 1217298-43-5 C₆₁H₆₅N₃O₈ 
• 1217298-45-7 C₆₁H₆₅N₃O₈ 
• 82659-57-2 3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)prop-1-ene 
• 321734-92-3 (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran 

Relevant articles and documents

Mild synthesis of protected α-D-glycosyl iodides

α-D-Glycosyl iodides are stereoselectively obtained by iodine replacement of the free anomeric hydroxyl group of fully protected sugars treated with a polymer bound triarylphosphane-iodine complex and imidazole. High yields and mild conditions, compatible

Thermal effect in β-selective glycosylation reactions using glycosyl iodides

The unique reactivity of glycosyl iodides and the fact that they react under neutral conditions makes them the donors of choice in our glycosylation strategies. Glycosyl iodides are generated in situ from either the anomeric acetate or the anomeric silyla

Unique reactions of glycosyl iodides with oxa- and thiocycloalkane acceptors

(Equation presented) Glucosyl-, galactosyl-, and mannosyl iodides efficiently react with strained oxacycloalkane acceptors to afford O-glycosides with high β-selectivity. The mechanism of ring opening was investigated by reacting mannosyl iodides with pur

Alpha-galactosylceramide analogs, a preparation method thereof, and a pharmaceutical composition for treatment and prevention of diseases by abnormal immune modulation comprising the same

The present invention refers to alpha - ceramide analogs, including manufacturing method of immunomodulatory or pharmaceutical composition for treating or preventing diseases caused and relates to, more particularly NKT intracellular Th1 or selective activation reaction Th2 can be effective for treating or preventing diseases caused immunomodulatory or alpha - ceramide analogs, and manufacturing method of including a pharmaceutical composition for treating or preventing diseases caused immunomodulatory or more are disclosed. (by machine translation)

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

Integrating ReSET with glycosyl iodide glycosylation in step-economy syntheses of tumor-associated carbohydrate antigens and immunogenic glycolipids

Carbohydrates mediate a wide range of biological processes, and understanding these events and how they might be influenced is a complex undertaking that requires access to pure glycoconjugates. The isolation of sufficient quantities of carbohydrates and glycolipids from biological samples remains a significant challenge that has redirected efforts toward chemical synthesis. However, progress toward complex glycoconjugate total synthesis has been slowed by the need for multiple protection and deprotection steps owing to the large number of similarly reactive hydroxyls in carbohydrates. Two methodologies, regioselective silyl exchange technology (ReSET) and glycosyl iodide glycosylation have now been integrated to streamline the synthesis of the globo series trisaccharides (globotriaose and isoglobotriaose) and α-lactosylceramide (α-LacCer). These glycoconjugates include tumor-associated carbohydrate antigens (TACAs) and immunostimulatory glycolipids that hold promise as immunotherapeutics. Beyond the utility of the step-economy syntheses afforded by this synthetic platform, the studies also reveal a unique electronic interplay between acetate and silyl ether protecting groups. Incorporation of acetates proximal to silyl ethers attenuates their reactivity while reducing undesirable side reactions. This phenomenon can be used to fine-tune the reactivity of silylated/acetylated sugar building blocks.

Concise synthesis of α-galactosyl ceramide from d-galactosyl iodide and d-lyxose

α-Galactosyl ceramide is synthesized from d-lyxose in 32% overall yield in five steps. The short and efficient protocol involves a one-pot protection and glycosidation of d-lyxose with d-galactosyl iodide as a key step. The α-linked disaccharide obtained was subsequently transformed into α-galactosyl ceramide in four steps involving Z-selective Wittig olefination at C-1, stereo-inversion at C-4 using azide, one-pot reduction of azide and amidation, and global deprotection.

Synthesis and biological evaluation of α-galactosylceramide analogues with heteroaromatic rings and varying positions of a phenyl group in the sphingosine backbone

We designed and synthesized seven α-GalCer analogues with a pyrazole moiety and varying positions of a phenyl group in the sphingosine backbone to polarize cytokine secretion. On the basis of in vitro and in vivo biological evaluations, we found that anal

Synthesis of β-C-galactosyl d- and l-alanines

Synthesis of β-C-d-galactosyl d- and l-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and SN2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.

Heteroaromatic moieties in the sphingosine backbone of α- Galactosylceramides for noncovalent interactions with CD1d

A series of α-GalCer analogues containing heterocyclic and aromatic moieties in the sphingosine backbone were synthesized to improve the selectivity in the Th1/Th2 cytokine profile via noncovalent interaction with three aromatic residues at the binding pocket of CD1d. In vitro and in vivo biological evaluations revealed the treatment of α-GalCer analogue (6) induced the selective stimulation of natural killer T cells to facilitate the secretion of Th2 cytokines.