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[ CAS No. 4099-85-8 ] {[proInfo.proName]}

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Chemical Structure| 4099-85-8
Chemical Structure| 4099-85-8
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Product Details of [ 4099-85-8 ]

CAS No. :4099-85-8 MDL No. :MFCD00270040
Formula : C9H16O5 Boiling Point : -
Linear Structure Formula :- InChI Key :DXBHDBLZPXQALN-WCTZXXKLSA-N
M.W : 204.22 Pubchem ID :96666
Synonyms :

Calculated chemistry of [ 4099-85-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.69
TPSA : 57.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : -0.42
Log Po/w (WLOGP) : -0.13
Log Po/w (MLOGP) : -0.53
Log Po/w (SILICOS-IT) : 0.22
Consensus Log Po/w : 0.26

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.71
Solubility : 39.9 mg/ml ; 0.195 mol/l
Class : Very soluble
Log S (Ali) : -0.32
Solubility : 98.8 mg/ml ; 0.484 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.29
Solubility : 105.0 mg/ml ; 0.516 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.29

Safety of [ 4099-85-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4099-85-8 ]

* 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 [ 4099-85-8 ]
  • Downstream synthetic route of [ 4099-85-8 ]

[ 4099-85-8 ] Synthesis Path-Upstream   1~59

  • 1
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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
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  • [ 77-76-9 ]
  • [ 67-64-1 ]
  • [ 4099-85-8 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride In methanol at 20℃; A solution of 50.0 g (0.34 mole) of dry D-ribose in 1.0 L of acetone, 100 mL of 2,2-dimethoxypropane, 200 mL of methanol containing 20 mL of methanol saturated with hydrogen chloride at 0° C. was stirred overnight at room temperature. The resulting solution was neutralized with pyridine and evaporated under reduced pressure. The resulting oil was partitioned between 400 mL of water and 400 mL of methylene chloride. The water layer was extracted twice with methylene chloride (400 mL). The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography [cluent: stepwise gradient of methanol (1-2percent) in methylene chloride] to give pure 1 (52.1 g, 75percent) as a yellow syrup. 1H-NMR (CDCl3): δ5.00 (s, 1H, H-1), 4.86 (d, 1H, H-2, J2-3=5.9 Hz), 4.61 (d, 1H, H-3, J3-2=5.9 Hz), 4.46 (t, 1H, H-4, J4-5=2.7 Hz), 3.77-3.61 (m, 2H, H-5 and H-5'), 3.46 (s, 1H, OCH3), 3.0-2.4 (br s, 1H, OH-5), 1.51 (s, 3H CH3), 1.34 (s, 3H CH3); MS (matrix GT): FAB>0 m/z 173 (M-OCH3)+.
Reference: [1] Patent: US2004/6007, 2004, A1, . Location in patent: Page/Page column 18; sheet 2
[2] Journal of Biological Chemistry, 1934, vol. 104, p. 299,302[3] Journal of Biological Chemistry, 1934, vol. 106, p. 421,425
[4] Journal of Heterocyclic Chemistry, 1966, vol. 3, p. 485,487
[5] Journal of Organic Chemistry, 1961, vol. 26, p. 2821,2826
  • 3
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YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride In acetone at 0 - 20℃; A solution of 50.0 g (0.34 mol) of dehydrated D-ribose in acetone (1.0 liter), 2,2-dimethoxypropane (100 mL), methanol (20 mL) containing 20 mL of methanol saturated with hydrogen chloride at 0 ° C. And the mixture was stirred overnight at room temperature. The resulting solution was neutralized with pyridine and the solvent was distilled off under reduced pressure. The resulting oil was fractionated between 400 mL of water and 400 mL of methylene chloride. The aqueous layer was extracted twice with methylene chloride (400 mL). The combined organic extracts were dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [eluent: methanol (1percent to 2percent) / stepwise gradient of methylene chloride] to give pure 1 (52.1 g, 75percent) as a yellow syrup.
Reference: [1] Journal of medicinal chemistry, 2001, vol. 44, # 18, p. 2966 - 2975
[2] Patent: JP2015/205885, 2015, A, . Location in patent: Paragraph 0443; 0444
[3] Organic Letters, 2007, vol. 9, # 6, p. 1121 - 1124
  • 4
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YieldReaction ConditionsOperation in experiment
51.1% With hydrogenchloride In water for 3 h; Reflux For 3000 ml three-mouth bottle adding 300gD - ribose, 1040 ml acetone, 1040 ml methanol, 30 ml concentrated hydrochloric acid, stirring and heating to reflux. Keep the backflow reaction 3h, cooling to room temperature, adding 450 ml purified water, saturated Na2 CO3 Solution to adjust the pH to 8 the left and the right, successively 600 ml ethyl acetate and 1200 ml ethyl acetate. The combined ethyl acetate, saturated salt water and water all washed, dried with anhydrous sodium sulfate 1h, filtered, distilled under reduced pressure to dry, can get 208.1g light yellow oily compound I, yield 51.1percent.
Reference: [1] Carbohydrate Research, 2003, vol. 338, # 4, p. 303 - 306
[2] Tetrahedron Letters, 1998, vol. 39, # 5-6, p. 385 - 388
[3] Russian Journal of Organic Chemistry, 2007, vol. 43, # 5, p. 742 - 746
[4] Heterocycles, 2014, vol. 8, # 2, p. 1519 - 1526
[5] Patent: CN106279095, 2017, A, . Location in patent: Paragraph 0017; 0040
[6] Chemical Communications, 2011, vol. 47, # 21, p. 6015 - 6017
[7] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 293 - 297
[8] Organic Process Research and Development, 2016, vol. 20, # 3, p. 609 - 614
  • 5
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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 16 h; 1) Obtaining Methyl 2,3-O-isopropyliden-β-D-ribofuranoside (5) A suspension of D-ribose (4, 10g) in acetone (80 mL) cooled to 0°C was added drop by drop to 2,2-dimethyoxypropane (20 mL) with perchloric acid 70percent (4 mL). It was stirred for two hours at ambient temperature and then methanol (14 mL) was added and the mixture was stirred at ambient temperature for 16 hours. A saturated solution of K2CO3 (10 mL) was added and the mixture was partitioned in water (150 mL) and CH2Cl2 (70 mL). The aqueous phase was extracted with CH2Cl2 (3 x 70 mL). The combined organic phases were dried (Na2SO4) and the solvent was evaporated to obtain 13,5 g of compound 5 as a colorless syrup. This same reaction was carried out starting from 20 g of D-ribose, obtaining the desired product with a 100percent yield.
Reference: [1] Patent: EP2241556, 2010, A1, . Location in patent: Page/Page column 8
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053
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YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride In methanol; dichloromethane; water; acetone Example 1
Preparation of 1-O-Methyl-2,3-O-isopropylidene-β-D-ribofuranose (1)
The title compound can be prepared according to a published procedure (Leonard, N. J.; Carraway, K. L. "5-Amino-5-deoxyribose derivatives.
Synthesis and use in the preparation of "reversed" nucleosides" J. Heterocycl. Chem. 1966, 3, 485-489).
A solution of 50.0 g (0.34 mole) of dry D-ribose in 1.0 L of acetone, 100 mL of 2,2-dimethoxypropane, 200 mL of methanol containing 20 mL of methanol saturated with hydrogen chloride at 0° C. was stirred overnight at room temperature.
The resulting solution was neutralized with pyridine and evaporated under reduced pressure.
The resulting oil was partitioned between 400 mL of water and 400 mL of methylene chloride.
The water layer was extracted twice with methylene chloride (400 mL).
The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure.
The residue was purified by silica gel column chromatography [eluent:
stepwise gradient of methanol (1-2percent) in methylene chloride] to give pure 1 (52.1 g, 75percent) as a yellow syrup. 1H-NMR (CDCl3): δ5.00 (s, 1H, H-1), 4.86 (d, 1H, H-2, J2-3=5.9 Hz), 4.61 (d, 1H, H-3, J3-2=5.9 Hz), 4.46 (t, 1H, H-4, J4-5=2.7 Hz), 3.77-3.61 (m, 2H, H-5 and H-5'), 3.46 (s, 1H, OCH3), 3.0-2.4 (br s, 1H, OH-5),1.51 (s, 3H CH3), 1.34 (s, 3H CH3); MS (matrix GT): FAB>0 m/z 173 (M-OCH3)+.
88% With pyridine; hydrogenchloride In methanol; acetone b.
Synthetic Method
Methyl 2,3-O-isopropylidene-β-D-ribofuranoside (202)
D-Ribose (25 g, 0.17 moles) was dissolved in 500 mL acetone containing 50 mL of 2,2-dimethoxypropane and 90 mL methanol.
10 mL of methanol saturated with HCl at 0° C. was added and the mixture was stirred at room temperature overnight.
The mixture was neutralized with the addition of 15 mL pyridine and partitioned between 500 mL H2 O and 200 mL ether.
The layers were separated and the aqueous layer extracted with two more 200 mL ether portions.
The ether layers were then dried and concentrated under reduced pressure to give 29.6 g(88percent) of methyl 2,3,-O-isopropylidene-β-D-ribofuranoside. 1 H NMR (DMSO-d6): δ 5.47 ppm (s, 1H, H-1), 5.32 (d, 1H, H-2), 5.08 (d, 1H, H-3), 4.92 (t, 1H, H-4), 4.14 (dq, 2H, H-5), 3.94 (s, 3H, OCH 3), 1.98 (s, 3H, Me), 1.81 (s, 3H, Me).
13 C NMR (DMSO-d6): δ 112.06, 109.89, 88.25, 85.72, 81.44, 63.88, 55.35, 26.28, 24.65.
Reference: [1] Patent: US2004/6002, 2004, A1,
[2] Patent: US5360795, 1994, A,
  • 7
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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
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In water; ethyl acetate at 0℃; for 0.5 h; Inert atmosphere
Stage #2: With hydrogenchloride; sodium chlorite In water; ethyl acetate at 20℃; for 7 h;
KBr (1.70 g, 14.7 mmol) and TEMPO (0.383 g, 2.45 mmol) were added to a solution of 2 (10.0 g, 49.0 mmol) in EtOAc (100 mL), followed by dropwise addition of NaOCl (12percent, 39.5 mL, 63.7 mmol) over 30 min at 0 °C. Then, the pH was adjusted to 2 by the addition of 35percent HCl, followed by the addition of 25percent aq NaClO2 (5.76 g, 63.7 mmol) over 30 min maintaining r.t. Stirring was continued until completion of the reaction after 7 h. After adjusting the pH to 2–3, the product was extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered, and the solvent was removed in vacuo to give the crude product. Recrystallization from hot CH2Cl2 with n-hexane gave a white solid; yield: 10.68 g (quant.); mp 128.5–129.5 °C (Lit.27b mp 129–131 °C); [α]D20.5 –67.29 (c 2.47, CHCl3).1H NMR (CDCl3, 400 MHz): δ = 10.69 (s, 1 H), 5.20 (d, J = 6.3 Hz, 1 H)5.09 (s, 1 H), 4.69 (s, 1 H), 4.59 (d, J = 6.0 Hz, 1 H), 3.45 (s, 3 H), 1.50(s,3 H), 1.34 (s, 3 H).
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