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[ CAS No. 4451-36-9 ] {[proInfo.proName]}

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Chemical Structure| 4451-36-9
Chemical Structure| 4451-36-9
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Product Details of [ 4451-36-9 ]

CAS No. :4451-36-9 MDL No. :MFCD00047514
Formula : C14H19ClO9 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 366.75 Pubchem ID :-
Synonyms :

Safety of [ 4451-36-9 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4451-36-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4451-36-9 ]

[ 4451-36-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 604-69-3 ]
  • [ 4451-36-9 ]
YieldReaction ConditionsOperation in experiment
91% With thionyl chloride; acetic acid In dichloromethane for 18h; Ambient temperature;
91% With thionyl chloride; acetic acid In dichloromethane for 18h; Ambient temperature; reactivity and stereospecificity; other acid, other solvents; other 1,2-trans-aldose peracetates;
90% With phosphorus pentachloride In dichloromethane for 0.0833333h;
90% With phosphorus pentachloride; boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; 1 4.2.2. Floyd's pathway NaOAc (1.58 g, 19.27 mmol) was suspended in Ac2O (21 mL,222 mol) and the resulting mixturewas heated to reflux for 20 min.The heating bathwas removed and D-glucose 2 (3.17 g,17.55 mmol)was added in small portions, keeping the reaction mixture just atreflux temperature. Subsequently, the mixture was stirred for anadditional 15 min under heating and, after cooling to rt, it waspoured onto crushed ice (80 mL). After keeping mixture in therefrigerator at 4C for 3 h, the resulting precipitate was filtered andwashed with ice-water (125 mL) and cold EtOH (10 mL). Afterdrying under reduced pressure, the crude product was recrystallisedfrom EtOH (20 mL) to yield 1,2,3,4,6-penta-O-acetyl-b-Dglucopyranoside6 (6.71 g, 98%). To pentaacetyl-b-D-glucopyranose6 (6.71 g, 17.2 mmol) and phosphorus pentachloride (3.89 g,18.92 mmol) in DCM (50 mL) in an atmosphere of argon was addedBF3.Et2O (25 ml). The reaction was stirring for 30 min at rt in anatmosphere of argon (monitoring by TLC), and thenwas partitionedbetween DCM (50 mL) and H2O (100 mL). The aqueous phase wasre-extracted with DCM (2 40 mL). The combined organics werewashed with sodium hydrogen carbonate (100 mL), brine (100 mL),dried over MgSO4, filtered and concentrated in vacuo. The resultingsolid was co-evaporated with toluene, triturated under cyclohexaneand crystallized from diethyl ether/petrol to afford 2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl chloride 7 (5.67 g, 90%) as awhite crystalline solid. To a solution of 2,3,4,6-tetra-O-acetyl-b-Dglucopyranosylchloride 7 (5.67 g, 15.48 mmol) in DMPU (15 mL) at0 C under an atmosphere of argon was added potassium thioacetate(2.32 g, 17.05 mmol). The reaction mixturewas stirring for 3days under an atmosphere of argon at 0 C (monitoring by TLC) andthen was partitioned between ethyl acetate (50 mL) and H2O(50 mL). After extraction with EtOAc (3 50 mL), the organic layerswere washed with brine, dried over MgSO4, filtered and concentratedin vacuo. The resulting residue was purified by silica gelchromatography eluting with 70% hexane/EtOAc to afford 1-Sacetyl-2,3,4,6-tetra-O-acetyl-1-thio-a-D-glucopyranoside 8 (3.96 g,63%) as a peach-coloured solid. A mixture of 8 (3.96 g, 9.76 mmol)and phenylmercuric acetate (3.48 g, 10.24 mmol) in absoluteethanol (40 mL) was boiled under reflux for 2 h. The resulting black precipitate was filtered off (Celite). The filtrate was evaporated todryness on a rotary evaporator and the resulting syrup was purifiedby column chromatography eluting with 60% hexane/EtOAc to yield9 (3.19 g, 51%) as a solid foam. Hydrogen sulfide was bubbled for20 min into a solution of 2,3,4,6-tetra-O-acetyl-1-phenylmercury(II)-thio-a-D-glucopyranose 9 (3.19 g, 4.98 mmol)in EtOH at 55 C. The resulting precipitatewas removed by filtrationand the filtrate was purified by column chromatography elutingwith 60% hexane/EtOAc.
49% With phosphorus pentachloride; boron trifluoride diethyl etherate In dichloromethane for 0.0833333h; Inert atmosphere;
With hydrogenchloride; acetyl chloride anfangs bei -70grad;
With hydrogenchloride; diethyl ether
With aluminium trichloride; chloroform
With titanium tetrachloride; benzene
With hydrogenchloride; phosphorus trichloride at 90℃;
With aluminium trichloride In chloroform; benzene for 0.5h; Ambient temperature;
With hydrogenchloride In dichloromethane at 0℃; for 2.5h;
With aluminium trichloride In chloroform
In dichloromethane for 2h;
12 g Stage #1: β-D-glucose pentaacetate With aluminum (III) chloride In chloroform at 20℃; Stage #2: With silicic acid In toluene
With phosphorus pentachloride; boron trifluoride diethyl etherate In dichloromethane for 0.333333h;
With aluminum (III) chloride In benzene
With aluminum (III) chloride In dichloromethane for 2h;

Reference: [1]Chittenden, Gordon J. F. [Carbohydrate Research, 1993, vol. 242, p. 297 - 302]
[2]Chittenden, Gordon J. F. [Carbohydrate Research, 1993, vol. 242, p. 297 - 302]
[3]Ibatullin, Farid M.; Selivanov, Stanislav I. [Tetrahedron Letters, 2002, vol. 43, # 52, p. 9577 - 9580]
[4]Vo, Quan V.; Rochfort, Simone; Nam, Pham C.; Nguyen, Tuan L.; Nguyen, Trung T.; Mechler, Adam [Carbohydrate Research, 2018, vol. 455, p. 45 - 53]
[5]Floyd, Nicola; Vijayakrishnan, Balakumar; Koeppe, Julia R.; Davis, Benjamin G. [Angewandte Chemie - International Edition, 2009, vol. 48, # 42, p. 7798 - 7802]
[6]Korytnyk; Mills [Journal of the Chemical Society, 1959, p. 636,644]
[7]Fox; Goodman [Journal of the American Chemical Society, 1950, vol. 72, p. 3256]
[8]Zemplen et al. [Acta Chimica Academiae Scientiarum Hungaricae, 1954, vol. 4, p. 73,75]
[9]Lemieux; Brice [Canadian Journal of Chemistry, 1955, vol. 33, p. 109,116, 117]
[10]de Pascual Teresa; Garrido Espinosa [Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1956, vol. 52, p. 347,456]
[11]Lichtenthaler, Frieder W.; Roenninger, Stephan; Kreis, Uwe [Liebigs Annalen der Chemie, 1990, # 10, p. 1001 - 1006]
[12]Tarumi; Takebayashi; Atsumi [Journal of Heterocyclic Chemistry, 1984, vol. 21, # 3, p. 849 - 854]
[13]Praly, J. P.; Descotes, G. [Tetrahedron Letters, 1987, vol. 28, # 13, p. 1405 - 1408]
[14]Blanc-Muesser, Michele; Defaye, Jacques; Driguez, Hugues [Journal of the Chemical Society. Perkin transactions I, 1982, p. 15 - 18]
[15]Bianchi, Aldo; Bernardi, Anna [Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4565 - 4577]
[16]Current Patent Assignee: 3M CO - US6372895, 2002, B1 Location in patent: Example 4
[17]Deobald, Anna M.; Camargo, Leandro R. S.; Alves, Diego; Zukerman-Schpector, Julio; Correa, Arlene G.; Paixao, Marcio W. [Synthesis, 2011, # 24, p. 4003 - 4010]
[18]Ichikawa, Yoshiyasu; Minami, Takahiro; Kusaba, Shohei; Saeki, Nobuyoshi; Tonegawa, Yuta; Tomita, Yumiko; Nakano, Keiji; Kotsuki, Hiyoshizo; Masuda, Toshiya [Organic and Biomolecular Chemistry, 2014, vol. 12, # 23, p. 3924 - 3931]
[19]Ghirardello, Mattia; Perrone, Daniela; Chinaglia, Nicola; Sádaba, David; Delso, Ignacio; Tejero, Tomas; Marchesi, Elena; Fogagnolo, Marco; Rafie, Karim; van Aalten, Daan M. F.; Merino, Pedro [Chemistry - A European Journal, 2018, vol. 24, # 28, p. 7264 - 7272]
  • 2
  • [ 59-02-9 ]
  • [ 4451-36-9 ]
  • 3,4,6‑tri‑O‑acetyl‑1,2‑O‑(1‑tocopheroxyethylidene)‑α‑D-glucopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% General procedure: To a solution of alpha-bromide 8alpha (1 mmol) and chloride 9alphaor 9beta (see Table 1, entries 11 and 12) in 4 cm3, anhydrousCH2Cl2was added TBAI (1 mmol) or TEABr (1 mmol)(see Table 1, entries 9 and 10) and 50 mg of MS 4A underan argon atmosphere at room temperature. The mixturewas stirred for 10 min, and a solution of phenol 1, 2, or3 (1 mmol) and DIPEA (1 mmol) in 2 cm3 of anhydrousCH2Cl2was added. The reaction mixture was refluxed for24 h, filtered through a Celite pad, and concentrated invacuo. The solid residue was redissolved in 10 cm3 CH2Cl2,washed with water and a solution of saturated NaHCO3,dried over anhydrous Na2SO4,and concentrated undervacuum. The crude product was purified by MPLC chromatographyand eluted with ethyl acetate-hexane to obtainorthoesters 10, 12, or 13. 3,4,6-Tri-O-acetyl-1,2-O-(1-tocopheroxyethylidene)-alpha-dglucopyranose(10, C43H68O11)Oil. 1H NMR (400 MHz,CDCl3):delta = 5.17 (d, 3J = 5.5 Hz, 1H, H-1?), 5.03-5.00 (m,1H, H-3?), 4.81 (dd, 3J = 2.4, 9.4 Hz, 1H, H-4?), 4.18-4.17(m, 2H, H-6?), 3.90-3.88 (m, 1H, H-5?), 3.66-3.60 (m,1H, H-2?), 2.57 (t, 3J = 6.6 Hz, 2H, H-4), 2.19, 2.16, 2.07(3xs, 9H, H-5a, 7a, 8b), 2.09, 2.05 (2xs, 9H, CH3CO),1.87 (s, 3H, H-8?), 1.80-1.78 (m, 2H, H-3), 1.40-1.21(m, 21H, H-1?-12?), 0.89-0.83 (m, 12H, H-4?a, 8?a, 12?a,13?) ppm; 13C NMR (100 MHz, CDCl3):delta = 170.6, 169.6,169.1 (CH3CO), 148.5 (C-8a), 141.9 (C-6), 130.0 (C-7),128.3 (C-8) 124.3 (C-7?), 123.0 (C-5), 117.8 (C-4a), 96.9(C-1?), 75.0 (C-2), 73.8 (C-2?), 70.4 (C-3?), 67.9 (C-4?),67.0 (C-5?), 63.1 (C-6?), 31.4 (C-3), 23.8 (C-8?), 22.7, 22.6(C-2a), 20.6 (C-4), 20.7 (CH3CO), 14.4, 13.6, 11.8 (C-5a,7a, 8b), and phytyl chain signals: 40.2, 39.3, 37.3-37.6,32.8, 32.7, 31.4, 27.9, 24.8, 24.4, 23.5, 23.3, 21.0, 19.7-19.6 ppm; IR (CHCl3) v= 2928, 2869, 1744, 1461, 1371,1232, 1087, 1040, 1002, 946, 907 cm-1; HRMS (ESI): calcdfor C43H68NaO11783.4659, found 783.4613.
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