Aryl 4,6-O-arylidene-1-thio-β-d-glycopyranoside-based new organogelators and their gels

Roy, Soumik; Chakraborty, Arijit; Ghosh, Rina

doi:10.1016/j.carres.2008.06.005

Cited by 21 publications

(5 citation statements)

References 48 publications

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“…The corresponding trichloroacetimidate 19 was prepared by chemoselective hydrolysis of the anomeric phenylsulfenyl group in 18 , followed by treatment with Cl 3 CCN and DBU. Similarly, the 4,6- O - p -anisilidene acetal of galactose, 20 , was converted into thioglycoside 23 and trichloroacetimidate 24 by the above-mentioned reaction sequence.…”

Section: Resultsmentioning

confidence: 99%

“…The organic layer was dried over Na 2 SO 4 , filtered off, and concentrated. The resulting residue was purified by flash column chromatography on silica gel using toluene/CHCl 3 (1:1) as the eluent to give 16 (2.44 g, 81%) as a yellow solid: 2, 134.7, 134.2, 133.0, 133.0, 132.9, 132.2, 130.6, 129.7, 129.0, 129.0, 128.5, 128.2, 127.8, 127.7, 127.6, 127.3, 126.5, 126.3, 125.3, 113.6, 101.7, 87.7, 81.2, 79.4, 78.7, 73.0, 72.0, 70.4, 68.6, 55.3 (18). To a solution of 16 (1.70 g, 3.14 mmol) in CH 2 Cl 2 (31.0 mL) was added 4 Å molecular sieves (1.70 g).…”

Section: ■ Conclusionmentioning

confidence: 99%

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Stereoselective Synthesis of Diglycosyl Diacylglycerols with Glycosyl Donors Bearing a β-Stereodirecting 2,3-Naphthalenedimethyl Protecting Group

et al. 2020

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Diglycosyl diacylglycerols (DGDGs) are major components of Gram-positive bacterial plasma membranes and are involved in the immune response systems. The chemical synthesis of DGDGs has been highly demanded, as it will allow the elucidation of their biological functions at the molecular level. In this study, we have developed a novel β-stereodirecting 2,3-naphthalenedimethyl (NapDM) protecting group that is orthogonal to protecting groups commonly used in oligosaccharide synthesis. The NapDM group can be easily cleaved under TFA-mediated acidic conditions. Futhermore, we demonstrated the application of this protecting group to an acyl protecting-group-free strategy by utilizing the NapDM group for the synthesis of DGDGs. This strategy features the use of the βstereodirecting NapDM group as an acid-cleavable permanent protecting group and late-stage glycosylation of monoglycosyl diacylglycerol acceptors, enabling the stereoselective synthesis of three different bacterial DGDGs with unsaturated fatty acid chain(s).

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Section: Resultsmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Stereoselective Synthesis of Diglycosyl Diacylglycerols with Glycosyl Donors Bearing a β-Stereodirecting 2,3-Naphthalenedimethyl Protecting Group

et al. 2020

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“…Ethyl 4,6‐ O ‐( p ‐methoxy)benzylidene‐1‐thio‐β‐ D ‐glucopyranoside (19): 24 Eluted with dichloromethane/methanol from 100:0 to 90:10; foam; 1 H NMR (400 MHz, CDCl 3 ): δ =7.40 and 6.84 (2×d, J =8.4 Hz, aromatic H, 4 H), 5.42 (s, 1 H), 4.36 (H‐1, d, J =10.0 Hz, 1 H), 4.24 (H‐6eq, dd, J =4.8, 10.4 Hz, 1 H), 3.75 (‐OCH 3 , s, 3 H), 3.75–3.60 (overlapped signals, 2 H), 3.50–3.30 (overlapped signals, 3 H), 2.68 (m, ‐SC H 2 CH 3 , 2 H), 1.26 (‐SCH 2 C H 3 , t, J =7.2 Hz, 3 H); 13 C NMR (100 MHz, CDCl 3 ): δ =160.0, 129.3 (aromatic C), 127.8, 113.7 (aromatic CH); 101.6 (acetal CH), 86.2 (C‐1), 80.1, 74.3, 73.1, 70.3, 68.4, 55.2, 24.5, 15.1; MALDI‐MS: m / z =365.30 [M+Na] + , calcd. for (C 16 H 22 O 6 S): 365.40; anal.…”

Section: Methodsmentioning

confidence: 99%

Three Solvent‐Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One‐Pot Generation of Orthogonally Protected Building Blocks

et al. 2015

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Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature. The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple experimental conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars

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“…26,29 Deacetylation of 10 with sodium methoxide and methanol produced 11 in quantitative yield. 27 The 4,6-benzylidene 12 was then installed with benzaldehyde/zinc chloride, 30 followed by the selective benzoylation of the C3 hydroxyl and the selective acetylation of the C4 -OH group to give 14 (13% over three steps). 31 Treatment with trifluoroacetic acid, then methyl pyruvate, led to replacement of the 4,6-benzylidene functionality with the pyruvate ester ketal (36% over 2 steps) and to the formation of 3.…”

Section: Organic Synthesis Of Tlr Ligandmentioning

confidence: 99%

Synthesis and immunological evaluation of a low molecular weight saccharide with TLR-4 agonist activity

Basava

Romlein

Bitsaktsis

et al. 2017

Bioorganic & Medicinal Chemistry

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The paucity of FDA approved adjuvants renders the synthesis, characterization, and use of new compounds as vaccine adjuvants, a necessity. For this purpose, a novel saccharide analog has been synthesized from glucosamine, pyruvylated galactose and 1,4-cyclohexanediol and its biological efficacy was determined in innate immune cells. More specifically, we assessed the production of pro-inflammatory cytokines from the murine monocyte cell line, Raw 264.7 and from C57 BL/6 mouse peritoneal macrophages following exposure to the saccharide analog. Our data conclude that the novel saccharide has immunostimulatory activity on mouse macrophages as indicated by the elevated levels of IL-6 and TNF-α in culture supernatants. This effect was TLR-4-dependent but TLR-2-independent. Our data, suggest TLR-4 agonism; a key feature of vaccine adjuvants.

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Aryl 4,6-O-arylidene-1-thio-β-d-glycopyranoside-based new organogelators and their gels

Cited by 21 publications

References 48 publications

Stereoselective Synthesis of Diglycosyl Diacylglycerols with Glycosyl Donors Bearing a β-Stereodirecting 2,3-Naphthalenedimethyl Protecting Group

Stereoselective Synthesis of Diglycosyl Diacylglycerols with Glycosyl Donors Bearing a β-Stereodirecting 2,3-Naphthalenedimethyl Protecting Group

Three Solvent‐Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One‐Pot Generation of Orthogonally Protected Building Blocks

Synthesis and immunological evaluation of a low molecular weight saccharide with TLR-4 agonist activity

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