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[ CAS No. 64363-77-5 ] {[proInfo.proName]}

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Chemical Structure| 64363-77-5
Chemical Structure| 64363-77-5
Structure of 64363-77-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 64363-77-5 ]

CAS No. :64363-77-5 MDL No. :MFCD23704947
Formula : C27H30O5 Boiling Point : -
Linear Structure Formula :- InChI Key :DJVKHGGGJZLGII-YGENNMJRSA-N
M.W : 434.52 Pubchem ID :11015594
Synonyms :

Calculated chemistry of [ 64363-77-5 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.33
Num. rotatable bonds : 11
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 122.15
TPSA : 46.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.62
Log Po/w (XLOGP3) : 4.11
Log Po/w (WLOGP) : 4.29
Log Po/w (MLOGP) : 2.56
Log Po/w (SILICOS-IT) : 4.83
Consensus Log Po/w : 3.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.81
Solubility : 0.00667 mg/ml ; 0.0000154 mol/l
Class : Moderately soluble
Log S (Ali) : -4.79
Solubility : 0.00712 mg/ml ; 0.0000164 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.22
Solubility : 0.00000264 mg/ml ; 0.0000000061 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.93

Safety of [ 64363-77-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 64363-77-5 ]

* 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 [ 64363-77-5 ]
  • Downstream synthetic route of [ 64363-77-5 ]

[ 64363-77-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 1824-96-0 ]
  • [ 100-39-0 ]
  • [ 64363-77-5 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydride In N,N-dimethyl-formamide at 25℃; Cooling with ice 12 g (73.1 mmol) ribose glucoside (or galoside) was placed in a 250 mL eggplant flask, 160 mL of analytically pure DMF was added, and after adding 17 g of NaH under an ice bath, 38 mL of BnBr was slowly added dropwise, and slowly warmed up to room temperature for overnight. TLC traced the reaction to an end. The reaction was extracted slowly with the addition of methanol, then extracted with EA, washed with water, and Crude product column chromatographic separation (ΡΕ: ΕΑ = 15:1- 9: 1) to obatin compound (2R,4S)- 3,4- bis(benzyloxy)- 2- ((benzyloxy)methyl)- 5- methoxytetrahydrofuran (28·6 g, 65.8 mmol, 90percent).
84% With sodium hydride In tetrahydrofuran at 0 - 25℃; Sodium hydride (0.75 g, 18.3 mmol) was added to a solution of compound 1 (1 g, 6.1 mmol) in dry tetrahydrofuran (15 ml) at 0 °C. Then BnBr (2.2 ml, 18.3 mmol) was added dropwise over 10 minutes. Ice bath was removed after stirring for 0.5 h at 0 °C. The reaction mixture was stirred at 25 °C over night. The mixture was filtered by using diatomite. The filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate =15:1) to obtain compound 2 as a colorless syrup in 84percent yield.
75% With sodium hydride In DMF (N,N-dimethyl-formamide); mineral oil at 0 - 60℃; Compound 2 (150 g, 0.914 mole) was dissolved in dry N, N-dimethylformarnide (DMF, 1.5 L), under nitrogen, in a three necked flask equipped with a mechanical stirrer and an addition funnel. The solution was cooled to 0°C in an ice bath. NaH (220 g, 60percent dispersion in mineral oil, 5.48 mole, 6 eq.) was added in small portions taking care to control the reaction and avoid overheating. When all the NaH had been added, addition of benzyl bromide (650 mL, 5.48 mole, 6 eq. ) was initiated drop-wise via the addition funnel. When all the benzyl bromide had been added the reaction was allowed to come to room temperature and stirred for 5 hrs. The reaction was then heated to 60°C and stirred at this temperature overnight. The reaction was quenched with methanol, concentrated in vacua, and partitioned between ether and water. The ether layer was washed once with 10percent citric acid solution, once with saturated sodium bicarbonate solution and once with brine. The ether layer was dried over anhydrous sodium sulfate, and concentrated to a pale, yellow syrup. This syrup was dissolved in 5percent ethyl acetate in hexane and applied to a silica gel plug in a 2 L sintered glass funnel. 5percent ethyl acetate in hexane was used to elute the desired product in 2 L fractions. The target fractions were concentrated under reduced pressure to give compound 3 (300 g) in 75percent yield.
70%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1 h;
Stage #2: With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 25℃; for 11 h;
To a solution of 27-7 (20.0 g, 121.8 mmol) in DMF (200 mL) was added NaH (17.1 g, 426.4 mmol) at 0°C. The mixture was stirred at 0°C for 1 h. The resulting solution was treated with TBAI (4.50 g, 12.2 mmol) and BnBr (72.93 g, 426.4 mmol, 50.7 mL). The mixture was stirred at 25°C for 11 h. The mixture was diluted with water (200 mL) and quenched with saturated NH4Cl solution (100 mL). The resulting solution was extracted with EA (200 mL). The combined organic layers were washed twice with brine (200 mL) and dried over anhydrous Na2SO4. After concentrating under reduced pressure, the residue was applied onto a silica gel column with PE/EA (25:1 to 5:1) to give compound 27-8 ((2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran, 37.20 g, 70percent) as light yellow oil.

Reference: [1] Patent: CN104628681, 2017, B, . Location in patent: Paragraph 0022; 0025-0028
[2] Patent: WO2018/53706, 2018, A1, . Location in patent: Page/Page column 18; 19
[3] Patent: WO2005/27962, 2005, A1, . Location in patent: Page/Page column 70
[4] Patent: WO2018/31818, 2018, A2, . Location in patent: Paragraph 0415
[5] Tetrahedron Letters, 1993, vol. 34, # 45, p. 7327 - 7330
[6] Nucleosides and Nucleotides, 1994, vol. 13, # 1-3, p. 109 - 126
[7] Tetrahedron Letters, 1995, vol. 36, # 7, p. 1085 - 1088
[8] RSC Advances, 2014, vol. 4, # 22, p. 11023 - 11028
  • 2
  • [ 100-39-0 ]
  • [ 64363-77-5 ]
YieldReaction ConditionsOperation in experiment
63.3%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 5 - 20℃; for 1 h;
Stage #2: at 0 - 20℃; for 13 h;
Stage #3: With water In N,N-dimethyl-formamide
Step 2: To a slurry of NaH (65 g, 60percent, 1.626 mol) in DMF (200 mL) was added crude compound from Step 1 (72 g, 406.66 mmol) in DMF (800 mL) over a period of 0.5 h, maintaining the temperature below 5 0C. The anion formed was stirred at room temperature for 30 min. Benzyl bromide (219.1 g, 1280.9 mmol) was added dropwise over a period of 1 h maintaining temperature between 0-5 °C. The reaction was stirred at room temperature for 12 h (TLC analysis in 30percent ethyl acetate/hexane showed complete disappearance of starting material), was diluted with water (500 mL) and extracted with ethyl acetate (2 x 1 L). The combined organic extracts were washed twice with water (1 L), brine (500 mL), and dried over MgSO4 and filtered. The filtrate was concentrated under vacuum to furnish crude residue. The crude residue was purified by flash chromatography (silica gel 1 kg), eluting with ethyl acetate in hexanes to furnish 112 g (63.3percent) of desired product as an oil.1HNMR (DMSO-^): δ 7.36-7.27 (m, 15H), 4.92 (s, IH), 4.66-4.44 (m, 6H), 4.12-4.07 (m, IH), 3.97 (dd, J= 6.78 and 4.5 Hz, IH), 3.91 (d, J- 4.5 Hz, IH), 3.55 (dd, J= 10.73 and 3.4 Hz, IH), 3.42 (dd, J= 10.7 and 6.0 Hz, IH), 3.21 (s, 3H)..
Reference: [1] Patent: WO2006/50161, 2006, A2, . Location in patent: Page/Page column 57-58
  • 3
  • [ 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
  • 4
  • [ 1824-96-0 ]
  • [ 100-44-7 ]
  • [ 64363-77-5 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 16, p. 3009 - 3012
[2] Patent: US2013/225520, 2013, A1, . Location in patent: Paragraph 0042
[3] Patent: US2013/244968, 2013, A1, . Location in patent: Paragraph 0042
[4] Patent: CN108285438, 2018, A, . Location in patent: Paragraph 0020; 0021; 0022
  • 5
  • [ 532-20-7 ]
  • [ 64363-77-5 ]
Reference: [1] Patent: WO2018/31818, 2018, A2,
[2] Patent: WO2018/53706, 2018, A1,
[3] Patent: CN108285438, 2018, A,
  • 6
  • [ 50-69-1 ]
  • [ 64363-77-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 22, p. 11023 - 11028
  • 7
  • [ 67-56-1 ]
  • [ 50-69-1 ]
  • [ 100-39-0 ]
  • [ 64363-77-5 ]
Reference: [1] Nucleosides and Nucleotides, 1994, vol. 13, # 10, p. 2035 - 2050
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