130323-37-4

Upstream product

• 136656-50-3 (2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane 
• 100-39-0 benzyl bromide 
• 21193-75-9 D-galactal 
• 166021-01-8 1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol 
• 196703-96-5 3,4-di-O-benzyl-6-O-(triisopropylsilyl)-D-galactal 
• 4098-06-0 triacetyl-D-galactal 
• 124751-19-5 (2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol 
• 201800-34-2 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-galactal 

Downstream Products

• 130257-36-2 3,4-di-O-benzyl-6-O-(2-methoxyethoxymethyl)-D-galacal 
• 141054-99-1 1,6-anhydro-4-O-benzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose 
• 385422-26-4 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-glucal 
• 944064-93-1 O-(2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-3,4-di-O-benzyl-D-galactal 
• 944064-94-2 O-(2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-3,4-di-O-benzyl-2-deoxy-2-nitro-D-galactal 
• 944064-95-3 O-(2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-3,4-di-O-benzyl-2-deoxy-2-nitro-D-galactopyranosyl)-N-(t-butyloxycarbonyl)-L-serine tert-butyl ester 
• 944064-96-4 O-(2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-3,4-di-O-benzyl-2-deoxy-2-nitro-D-galactopyranosyl)-N-(t-butyloxycarbonyl)-L-serine tert-butyl ester 
• 1053708-40-9 C₆₁H₇₇N₃O₁₄ 
• 944064-98-6 O-(2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-3,4-di-O-benzyl-2-deoxy-2-nitro-D-galactopyranosyl)-N-(t-butyloxycarbonyl)-L-threonine tert-butyl ester 
• 944064-99-7 O-(2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-3,4-di-O-benzyl-2-deoxy-2-nitro-D-galactopyranosyl)-N-(t-butyloxycarbonyl)-L-threonine tert-butyl ester 
• 1416144-45-0 C₄₀H₄₉NO₁₆ 
• 1198096-97-7 C₄₀H₄₉NO₁₆ 

Relevant academic research and scientific papers

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.

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is

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

α-Selective organocatalytic synthesis of 2-deoxygalactosides

Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism. Copyright

Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis

(Chemical Equation Presented) A 3,4-O-unprotected galactal derivative having bulky 6-O-TIPS protection (compound 2) could be regioselectively 3-O-glycosylated with O-(galactopyranosyl) trichloroacetimidates; depending on the protecting group pattern stere

Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks

A linear synthesis of a fully protected H-type II blood group determinant pentasaccharide utilizing glycosyl phosphate and glycosyl trichloroacetimidate building blocks is reported. Envisioning an automated solid-phase synthesis of blood group determinants, the utility of glycosyl phosphates in the stepwise construction of complex oligosaccharides, such as the H-type II antigen, is demonstrated. Installation of the central glucosamine building block required the screening of a variety of nitrogen protecting groups to ensure good glucosamine donor reactivity and protecting group compatibility. The challenge to differentiate C2 of the terminal galactose in the presence of other hydroxyl and amine protecting groups prompted us to introduce the 2-(azidomethyl)benzoyl group as a novel mode of protection for carbohydrate synthesis. The compatibility of this group with traditionally employed protecting groups was examined, as well as its use as a C2 stereodirecting group in glycosylations. The application of the 2-(azidomethyl)benzoyl group along with a systematic evaluation of glycosyl donors allowed for the completion of the pentasaccharide and provides a synthetic strategy that is expected to be generally amenable to the solid support synthesis of blood group determinants.

A New General Route to the Synthesis of Bicyclic Synthons from Glycals

Iodonium sym-dicollidine perchlorate (IDCP: bis(2,4,6-trimethylpyridine)iodine(1+) perchlorate) mediated intramolecular iodoalkoxylation of 3,4-di-O-substituted glycals 9a-14f gives rise to synthetically useful chiral bicyclic synthons 15a-20f respectivel

Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate.

3,4,6-Tri-O-acetyl-D-galactal was transformed into methyl 6-O-acetyl-2-azido-4-O-benzyl-2-deoxy-beta-D-galactopyranoside and its 4-O-acetyl-6-O-benzyl analogue, each of which was glycosylated with activated, O-acetylated derivatives of methyl D-glucopyranosyluronate. The resulting beta-(1----3)-linked disaccharide derivatives were each reductively N-acetylated, hydrogenolysed, O-sulfated, and saponified to afford the disodium salts of methyl 2-acetamido-2-deoxy-3-O-(beta-D-glucopyranosyluronic acid)-4-O-sulfo-beta-D-galactopyranoside and the 6-O-sulfo analogue. D-Galactal was also transformed into activated derivatives of 2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose and their 3,4-di-O-benzyl analogues with various substituents at O-4 and O-6. These glycosyl donors were condensed with 6-O-protected derivatives of methyl 2,3-di-O-benzyl-beta-D-glucopyranoside to give the beta-(1----4)-linked disaccharide derivatives, which were selectively deprotected, then oxidised at C-6 of the gluco unit, reductively N-acetylated, selectively deprotected, O-sulfated at C-4 or C-6 of the galacto unit, and hydrogenolysed to give the disodium salts of methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranosyl)-beta-D- glucopyranosiduronic acid and the 6-O-sulfo analogue.