Use of Diphenylacetyl Chloride as Protective Reagent for Sugars

Santoyo-González, F.; Garcia‐Calvo‐Flores, F.; Isac‐García, Joaquín; Robles‐Diaz, R.; Vargas‐Berenguel, Antonio

doi:10.1055/s-1994-25413

Cited by 9 publications

(4 citation statements)

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“…Methyl 2,3,4-tri-O-acetyl-α-D-mannopyranoside (15). 30 Trityl chloride (3.64 g, 13.06 mmol) was added to a suspension of methyl-α-D-mannopyranoside (2.29 g, 11.79 mmol) in pyridine (35 mL) at 0 °C. The reaction was stirred at RT and 40 °C for 2 days.…”

Section: Oligosaccharide Inhibitionmentioning

confidence: 99%

“…Lit. 30 [α] D +50 (c 1.0, CHCl 3 ); IR ν 3512 (w, br), 2939 (w), 2841 (w), 1753 (s), 1434 (w), 1371 (s), 1227 (s), 1137 (s), 1087 (s), 1064 (s), 937 (m), 757 (w) (cm −1 ); 1 H NMR (600 MHz, CDCl 3 ) δ 5.40 (dd, 1H, J 2,3 = 3.5 Hz, J 3,4 = 10.2 Hz, H-3), 5.27-5.23 (m, 2H, H-2, H-4), 4.73 (d, 1H, J 1,2 = 1.7 Hz, H-1), 3.78-3.70 (m, 2H, H-5, H-6a), 3.66-3.62 (m, 1H, H-6b), 3.41 (s, 3H, OCH 3 ), 2.36 (dd, 1H, J OH,6a = 5.6 Hz, J OH,6b = 8.6 Hz, OH), 2.15 (s, 3H, COCH 3 ), 2.08 (s, 3H, COCH 3 ), 2.01 (s, 3H, COCH 3 ); 13 C NMR (125 MHz, CDCl 3 ) δ 170.8 (CvO); 170.1 (CvO), 169.9 (CvO), 98.6 (C-1), 70.5 (C-5), 69.6 (C-2), 68.9 (C-3), 66.5 (C-4), 61.3 (C-6), 55.3 (OCH 3 ), 20.9 (COCH 3 ), 20.73 (COCH 3 ), 20.70 (COCH 3 ); MS [ESI] calcd for C 13 H 20 O 9 Na 343.1 (M + Na) + , found 343.1. 16).…”

Section: Oligosaccharide Inhibitionmentioning

confidence: 99%

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Synthesis of a Candida albicans tetrasaccharide spanning the β1,2-mannan phosphodiester α-mannan junction

2012

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The cell wall phosphomannan of Candida species is a complex N-linked glycoprotein with a glycan chain containing predominantly an α-linked mannose backbone with α-mannose branches. A minor β-mannan component is attached to the branches either via a glycosidic bond (acid stable β-mannan) or a phosphodiester bond (acid-labile β-mannan). The α-mannan residues of the cell wall phosphomannan do not afford protective antibody, while the β-mannan portion is a protective antigen and has become an attractive target as the key epitope of a conjugate vaccine. We report the first synthesis of a tetrasaccharide 1 consisting of a β1,2-mannopyranosyl trisaccharide linked via a phosphodiester to methyl α-mannopyranoside. This encompasses the attachment site of the acid labile β-mannan to the α-mannan component of the cell wall phosphomannan. The trisaccharide was formed by an iterative process to first create a β-glucopyranoside linkage and then epimerize the C-2 center via an oxidation-reduction sequence. The phosphate diester linkage was accessed via an anomeric H-phosphonate. The binding of phosphomannan fragment 1 with the protective antibody C3.1 has been evaluated and compared with a β-mannotrioside in hapten inhibition experiments. The observed activities are rationalized with a model for docked in the binding site of C3.1.

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Section: Oligosaccharide Inhibitionmentioning

confidence: 99%

Section: Oligosaccharide Inhibitionmentioning

confidence: 99%

Synthesis of a Candida albicans tetrasaccharide spanning the β1,2-mannan phosphodiester α-mannan junction

2012

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“…Diphenylacetyl chloride ( 1 ) has been used as a reagent in regioselective acylations of cyclomalto‐oligosaccharides and in preparations of N ‐substituted amides having local anesthetic properties . It has a similar structure to benzoyl chloride and readily reacts with alcohols or water.…”

Section: Introductionmentioning

confidence: 99%

Correlation of Rates of Solvolysis of Diphenylacetyl Chloride Using Extended Grunwald–Winstein Equation

Koh

Kang

2015

Bulletin Korean Chem Soc

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“…Esters are important protecting groups in carbohydrate chemistry. [1][2][3][4][5][6] Selective acylation in carbohydrates is possible by the combination of the different reactivity of the hydroxy groups with the use of hindered carboxylic acid chlorides (such as pivaloyl chloride and diphenylacetyl chloride 7 ) or the use of less reactive esterifying reagents that transfer acyl groups (such as N -acyl imidazoles, 3,[8][9][10][11][12] benzoyl cyanide, 13,14 3-acylthiazolidine-2-diones and 3acyl-5-methyl-1,3,4-thiadiazole-2(3 H )-thiones [15][16][17]. Pivaloyl esters with their great steric hindrance can be formed very selectively with pivaloyl chloride in pyridine at low temperature.…”

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confidence: 99%