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Chemical Structure| 532-20-7
Chemical Structure| 532-20-7
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CAS No. :532-20-7 MDL No. :
Formula : C5H10O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 150.13 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 532-20-7 ]

* 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.

  • Upstream synthesis route of [ 532-20-7 ]
  • Downstream synthetic route of [ 532-20-7 ]

[ 532-20-7 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 67-56-1 ]
  • [ 532-20-7 ]
  • [ 67-64-1 ]
  • [ 4099-85-8 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 48 h; Inert atmosphere To a suspension of D-ribose (1; 20.0 g, 133.2 mmol) in acetone (100mL) and MeOH (100 mL) was carefully added conc. H2SO4 (10 mL) at r.t. The resulting solution was stirred for 48 h. After the completion of reaction by TLC monitoring, the solution was neutralized by the addition of solid NaHCO3. The solid was filtered, then the mixture was concentrated, and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The crude product was purified by silica gel flash column chromatography to give the product as a pale yellow oil; yield 24.4 g (90percent); Rf = 0.2 (hexane/EtOAc= 5:1, v/v); [α]D25 –80.00 (c 1.00, CHCl3) {Lit.26 [α]D20 –75.00 (c 1.00,CHCl3)}.1H NMR (CDCl3, 400 MHz): δ = 4.97 (s, 1 H), 4.83 (d, J = 5.7 Hz, 1 H),4.58 (d, J = 6.0 Hz, 1 H), 4.42 (t, J = 2.7 Hz, 1 H), 3.56–3.72 (m, 2 H),3.43 (s, 3 H), 3.32 (dd, J = 10.0, 3.0 Hz, 1 H), 1.49 (s, 3 H), 1.32 (s, 3 H).
46%
Stage #1: With hydrogenchloride In water for 1.5 h; Inert atmosphere; Reflux
Stage #2: With pyridine In water at 20℃; Inert atmosphere
Compound5 was prepared from D-ribose according to literature procedures.1D-ribose (6.987 g, 46.07 mmol) was dissolved in a60 mL solution of 1:1 methanol/acetone. Approximately1 mL of concentrated HCl was added dropwise before reaction was heated toreflux for 90 min. The reaction was monitoredby TLC (2:1 EtOAc/hexanes) and allowed to cool to room temperature uponconsumption of starting material. Thereaction mixture was neutralized with pyridine and concentrated by rotaryevaporation. The crude material was partitionedbetween ethyl acetate (40 mL) and water (100 mL). The aqueous layer was extracted with threeportions of ethyl acetate (40 mL), and the organic layers were combined andwashed with saturated aqueous CuSO4 (75 mL), two portions of dH2O(75 mL), one portion of brine (75 mL), and dried over MgSO4. After filtration, the product was concentratedby rotary evaporation. Product wasisolated as a light yellow oil after short-path distillation (4.299 g, 21.05mmol, 46percent) but crude material (5.738 g, 28.1 mmol, 60percent) was typically used toprepare sulfonates 8d and 8e.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 18, p. 4299 - 4302
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 20, p. 7972 - 7990
[3] Journal of the American Chemical Society, 2015, vol. 137, # 10, p. 3558 - 3564
[4] Organic and Biomolecular Chemistry, 2009, vol. 7, # 4, p. 761 - 776
[5] Journal of Fluorine Chemistry, 1993, vol. 60, # 2.3, p. 239 - 250
[6] Journal of Organic Chemistry, 1996, vol. 61, # 18, p. 6175 - 6182
[7] Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11226 - 11230[8] Angew. Chem., 2016, vol. 128, # 37, p. 11392 - 11396,5
[9] Carbohydrate Research, 2014, vol. 394, p. 32 - 38
[10] Carbohydrate Research, 2010, vol. 345, # 1, p. 41 - 44
[11] Organic Letters, 2011, vol. 13, # 7, p. 1594 - 1597
[12] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 6186 - 6200
[13] Synthesis (Germany), 2014, vol. 46, # 9, p. 1185 - 1190
[14] Patent: WO2018/167794, 2018, A1, . Location in patent: Page/Page column 62; 63
  • 2
  • [ 532-20-7 ]
  • [ 67-64-1 ]
  • [ 4099-85-8 ]
YieldReaction ConditionsOperation in experiment
80% With acetyl chloride In methanol for 12 h; Inert atmosphere; Reflux AcCl(95 µL, 1.33 mmol) was addeddropwise to a solution of d-ribose(2.00 g, 13.33 mmol) in MeOH (8.0 mL) and Me2CO (8.0 mL). Thesolution was then heated at reflux for 12 h. The reaction was then quenchedwith sat. NaHCO3 (5mL) and the organic solvents evaporated under reduced pressure. The aqueoussolution was then extracted with EtOAc (2×20 mL), and the combined organicwashings dried over MgSO4, filtered and concentrated under reducedpressure to afford the desired compound as a colourless oil (2.18 g, 80percent), which was deemed sufficiently pure(according to 1H NMR spectroscopy) to be used in the nextreaction without further purification. Rf = 0.45 (2:1 hexanes/EtOAc). 1HNMR (300 MHz, CDCl3)d 4.97 (s, 1H), 4.84 (d, J = 5.9 Hz, 1H), 4.59 (d, J =5.9 Hz, 1H), 4.44 (t, J = 2.6 Hz,1H), 3.70 (dt, J = 12.6, 2.4 Hz, 1H),3.62 (ddd, J = 12.6, 10.7, 3.4 Hz,1H), 3.44 (s, 3H), 3.23 (dd, J =10.7, 2.6 Hz, 1H), 1.49 (s, 3H), 1.32 (s, 3H). The spectral data matched those reported previously.
Reference: [1] Tetrahedron, 2013, vol. 69, # 49, p. 10581 - 10592
[2] ChemSusChem, 2018, vol. 11, # 1, p. 292 - 298
  • 3
  • [ 67-56-1 ]
  • [ 532-20-7 ]
  • [ 77-76-9 ]
  • [ 4099-85-8 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 16, p. 3089 - 3096
[2] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 11, p. 2027 - 2038
[3] Patent: WO2005/20933, 2005, A2, . Location in patent: Page/Page column 52
[4] Croatica Chemica Acta, 2015, vol. 88, # 1, p. 43 - 52
  • 4
  • [ 532-20-7 ]
  • [ 4099-85-8 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 20, p. 3461 - 3464
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053
[3] Carbohydrate Research, 1996, vol. 280, # 2, p. 209 - 221
[4] Chemistry--A European Journal, 2015, vol. 21, # 1, p. 126 - 135
  • 5
  • [ 67-56-1 ]
  • [ 532-20-7 ]
  • [ 4099-85-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 10079 - 10102
  • 6
  • [ 2627-69-2 ]
  • [ 532-20-7 ]
  • [ 360-97-4 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 14, p. 3113 - 3119
  • 7
  • [ 532-20-7 ]
  • [ 54622-95-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4299 - 4302
  • 8
  • [ 532-20-7 ]
  • [ 15384-34-6 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 42, p. 9989 - 9991
[2] Chemical Communications, 2017, vol. 53, # 75, p. 10362 - 10365
  • 9
  • [ 93135-56-9 ]
  • [ 13754-19-3 ]
  • [ 532-20-7 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 25, p. 4964 - 4969
  • 10
  • [ 550-33-4 ]
  • [ 13754-19-3 ]
  • [ 532-20-7 ]
  • [ 120-73-0 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1984, vol. 38, # 8, p. 673 - 678
  • 11
  • [ 532-20-7 ]
  • [ 22423-26-3 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 10, p. 1255 - 1256
[2] Journal of the Chemical Society, Chemical Communications, 1994, # 10, p. 1255 - 1256
  • 12
  • [ 532-20-7 ]
  • [ 100-39-0 ]
  • [ 68-12-2 ]
  • [ 64363-77-5 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 12 h; Cooling with ice 12 g (73.1mmol) of ribose was weighed and added to 250mL eggplant bottle, 160 mL of analytically pure DMF was added and 17g NaH was added in ice bath and 38 mL BnBr was dropped slowly. The temperature was slowly raised to room temperature, and reacted for 12 hours. After completion of the reaction by TLC, methanol was added slowly to extract the reaction and again extracted with EA, washed with water, and the crude product was chromatographed (PE: EA = 15: 1 → 9: 1) to give the compound (2R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran (28.6 g, 65.8 mmol, 90percent). The compound 38a (3.5 g, 8.0 mmol) was weighed into a 100 mL eggplant flask, 28 mL of 1,4-dioxane was added to dissolve it, and 28 mL of 4N HCl was added. The temperature was refluxed for 3 hours. After completion of the reaction tracked by TLC, the reaction mixture was extracted with EA, washed with water, and then washed with saturated NaHCO3 solution and saturated NaCl solution. The crude product was chromatographed under reduced pressure (PE: EA = 5: 1 → 3.5: 1) to obtain (3S,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol (2.9 g,6.9 mmol, 86percent).
Reference: [1] Patent: CN106167475, 2016, A, . Location in patent: Paragraph 0018-0024
  • 13
  • [ 532-20-7 ]
  • [ 64363-77-5 ]
Reference: [1] Patent: WO2018/31818, 2018, A2,
[2] Patent: WO2018/53706, 2018, A1,
[3] Patent: CN108285438, 2018, A,
  • 14
  • [ 532-20-7 ]
  • [ 108-24-7 ]
  • [ 28708-32-9 ]
YieldReaction ConditionsOperation in experiment
64% at 25℃; for 24 h; General procedure: Per-O-acetylation of natural carbohydrates catalyzed by pyridine followed literature procedure, with slight modifications.33 A mixture of the carbohydrate (1.0 mmol), Ac2O (1.9 mL; 20 mmol), and pyridine (3 mL) was stirred at 25 °C for 24 h. The reaction mixture was diluted with 5 mL of CH2Cl2 and the organic phase was washed with1 mol L-1 HCl (3 × 5 mL), saturated NaHCO3 (3 × 5 mL), and brine (5 mL). The solvent was dried with anhydrous Na2SO4 and evaporated to furnish the per-O-acetylated carbohydrate derivatives. Peracetylated carbohydrates where characterized as above and showed physical and spectral data in accordance with literature.37-41
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 29-30, p. 4491 - 4493
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 2713 - 2718
[3] Asian Journal of Chemistry, 2014, vol. 26, # 14, p. 4367 - 4369
[4] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 4, p. 755 - 764
[5] Organic and Biomolecular Chemistry, 2004, vol. 2, # 17, p. 2538 - 2546
[6] Organic Letters, 2010, vol. 12, # 20, p. 4624 - 4627
[7] Journal of the American Chemical Society, 2011, vol. 133, # 27, p. 10459 - 10472
  • 15
  • [ 532-20-7 ]
  • [ 108-24-7 ]
  • [ 28708-32-9 ]
  • [ 4627-30-9 ]
Reference: [1] Synthesis, 2009, # 11, p. 1834 - 1840
  • 16
  • [ 532-20-7 ]
  • [ 3387-36-8 ]
Reference: [1] Journal of the American Chemical Society, 1983, vol. 105, # 25, p. 7428 - 7435
  • 17
  • [ 532-20-7 ]
  • [ 162204-20-8 ]
Reference: [1] Patent: CN102212095, 2016, B,
  • 18
  • [ 532-20-7 ]
  • [ 274693-53-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3598 - 3602
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