53182-61-9

Upstream product

• 198338-59-9 methyl 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-mannopyranoside 
• 120200-51-3 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 127073-25-0 methyl 2,3,4-tri-O-benzoyl-6-O-bromoacetyl-α-D-mannopyranoside 
• 853879-39-7 benzoic acid 3,5-dibenzoxy-2-(tert-butyldimethylsilanyloxymethyl)-6-methoxytetrahydropyran-4-yl ester 
• 618-32-6 Benzoyl bromide 
• 127073-24-9 methyl 6-O-bromoacetyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 6605-40-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 98-88-4 benzoyl chloride 
• 74247-81-7 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside 
• 20231-36-1 methyl 6-O-trityl-α-D-mannopyranoside 
• 110319-39-6 methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 
• 127073-07-8 methyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranoside 
• 127073-06-7 methyl 6-O-bromoacetyl-β-D-galactopyranoside 

Downstream Products

• 172364-85-1 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 1263311-56-3 methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-galactopyranoside 
• 129199-11-7 methyl O-(2,4-di-O-benzoyl-3-deoxy-β-D-xylo-hexopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 131291-20-8 O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl chloride 
• 131291-24-2 methyl O-(2,3-di-O-benzoyl-4-deoxy-β-D-xylo-hexopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 130651-34-2 O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl ckloride 
• 143249-60-9 O-(2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl chloride 
• 108967-30-2 C₃₀H₂₇BrO₁₀ 
• 101802-77-1 2,3,4-tri-O-benzoyl-6-O-(bromoacetyl)-α-D-galactopyranosyl chloride 
• 101802-81-7 O-(2,3,4-tri-O-benzoyl-6-O-bromoacetyl-β-D-galactopyranosyl)-(1-6)-1,2,3,4-tetra-O-benzoyl-α-D-galactopyranose 
• 101802-82-8 O-(2,3,4-tri-O-benzoyl-6-O-bromoacetyl-β-D-galactopyranosyl)-(1-6)-1,2,3,4-tetra-O-benzoyl-β-D-galactopyranose 

Relevant academic research and scientific papers

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.

Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives

We applied a desilylation procedure using SO3H silica gel, with the surface modified by alkylsulfonic acid groups, to silylated sugar, nucleoside, and alkaloid derivatives. The treatment with SO3H silica gel provided desilylated products in good to excellent yield. In the reactions of sugar and nucleoside derivatives, no silyl residue was detected in the crude products, but the crude products of the reaction of alkaloids contained small amounts of silyl residues. Even though the sugar and nucleoside derivatives had a labile glycosyl and C–N bond, respectively, these bonds tolerated the reaction conditions. These outcomes suggested that the desilylation procedure using SO3H silica gel would be applicable to the deprotection of a variety of types of compounds protected by silyl groups. In a gram scale experiment, the desilylation procedure successfully proceeded without the observation of any silyl residue in the crude product.

Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica

A series of methoxy and deoxy derivatives of mannopyranose-1-phosphate (Manp-1P) were chemically synthesized, and their ability to be converted into the corresponding guanosine diphosphate mannopyranose (GDP-Manp) analogues by a pyrophosphorylase (GDP-ManPP) from Salmonella enterica was studied. Evaluation of methoxy analogues demonstrated that GDP-ManPP is intolerant of bulky substituents at the C-2, C-3, and C-4 positions, in turn suggesting that these positions are buried inside the enzyme active site. Additionally, both the 6-methoxy and 6-deoxy Manp-1P derivatives are good or moderate substrates for GDP-ManPP, thus indicating that the C-6 hydroxy group of the Manp-1P substrate is not required for binding to the enzyme. When taken into consideration with other previously published work, it appears that this enzyme has potential utility for the chemoenzymatic synthesis of GDP-Manp analogues, which are useful probes for studying enzymes that employ this sugar nucleotide as a substrate.

Synthesis and structure elucidation of benzoylated deoxyfluoropyranosides

Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful

Regioselective C-6 hydrolysis of methyl O-benzoyl-pyranosides catalysed by candida rugosa lipase

Hydrolysis of six methyl O-benzoyl-pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C-6, The rate of reaction was dependent on pyra

Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst

Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH 2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.

A facile, catalytic, and environmentally benign method for selective deprotection of teri-butyldimethylsilyl ether mediated by phosphomolybdic acid supported on silica gel

An environmentally benign PMA supported on SiO2 is found to be an efficient catalyst for the chemoselective deprotection of TBDMS ethers under very mild conditions. Various labile functional groups such as isopropylidene acetal, OTBDPS, OTHP, Oallyl, OBn, alkene, alkyne, OAc, OBz, N-Boc, N-Cbz, N-Fmoc, mesylate, and azide are found to be stable under the reaction conditions. This "truly catalytic" heterogeneous reaction does not require aqueous workup, and the supported catalyst and the solvent can be readily recovered and recycled.

A mild and efficient approach for the regioselective silyl-mediated protection-deprotection of C-4 hydroxyl group on carbohydrates

A regioselective route is reported, which makes the free 4-OH group of hexopyranoses and derivatives easily and rapidly available. This protocol shows high efficiency on intermediates, such as 1a, which contain a TIPS protective group at C-6 and necessarily a benzoyl group at C-4. Treatment of 1a with TBAF cleaves the TIPS protecting group and gives rise to an intramolecular migration of the benzoyl group at C-4 to the less crowded C-6 position.

Detritylation of mono- and di-saccharide derivatives using ferric chloride hydrate

Quantitative detritylation of mono- and di-saccharide derivatives of diverse structure was achieved with FeCl3 · 6H2O in CH2Cl2 at room temperature. Benzyl, isopropylidene, isopropylthio, allyl, acetyl, and benzoyl O-protecting groups were not effected under the designated conditions.

Synthesis of mono- and dimannoside phosphoramidite derivatives for solid-phase conjugation to oligonucleotides

Mannose and dimannose derivatives have been prepared with an anomerically-linked hydrophobic spacer, and converted to phoshoramidite derivatives suitable for conjugation to oligoribodeoxynucleotides on a DNA/RNA synthesizer. Synthesis of a monomannoside-linked 15-mer oligoribodeoxynucleotide is reported.