Home Cart 0 Sign in  

[ CAS No. 83159-91-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 83159-91-5
Chemical Structure| 83159-91-5
Structure of 83159-91-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 83159-91-5 ]

Related Doc. of [ 83159-91-5 ]

Alternatived Products of [ 83159-91-5 ]

Product Details of [ 83159-91-5 ]

CAS No. :83159-91-5 MDL No. :MFCD01630917
Formula : C17H36O4Si2 Boiling Point : -
Linear Structure Formula :- InChI Key :DCFHRVSQGCDCMH-UONOGXRCSA-N
M.W : 360.64 Pubchem ID :10761020
Synonyms :

Calculated chemistry of [ 83159-91-5 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.94
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 100.91
TPSA : 44.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.28
Log Po/w (XLOGP3) : 5.23
Log Po/w (WLOGP) : 4.71
Log Po/w (MLOGP) : 2.31
Log Po/w (SILICOS-IT) : 1.04
Consensus Log Po/w : 3.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.91
Solubility : 0.00445 mg/ml ; 0.0000123 mol/l
Class : Moderately soluble
Log S (Ali) : -5.92
Solubility : 0.000435 mg/ml ; 0.00000121 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.17
Solubility : 0.0242 mg/ml ; 0.000067 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.41

Safety of [ 83159-91-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 83159-91-5 ]

* 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.

  • Downstream synthetic route of [ 83159-91-5 ]

[ 83159-91-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 18162-48-6 ]
  • [ 34371-14-7 ]
  • [ 83159-91-5 ]
YieldReaction ConditionsOperation in experiment
96% With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20℃; for 18.0h;Inert atmosphere; In a 12L three-neck round bottom flask under nitrogen, (4S,5R)-4-hydroxy-5- (hydroxymethyl)dihydrofuran-2(3H)-one (366.4 g, 2773 mmol, 1 eq), imidazole (472 g, 6933 mmol, 2.5 eq) and DMF (2.5L) were charged and stirred at room temperature. At room temperature, TBSC1 (878 g, 5824 mmol, 2.1 eq) was added in portions over 10 minutes, due to an exotherm of 15C (25C to 40C). Then DMAP (16.94 g, 139 mmol, 0.05 eq) was added and mixture was allowed to stir at room temperature for 18 hours. Reaction completion was monitored by TLC (Eluent: 15% MTBE I 0.5% Et3N I 84.5% heptane). At room temperature, H20 (5.0 L) was charged to the reaction mixture and allowed to stir for 30 minutes. The solids where filtered through a Buchner Funnel (6.0 L, fine frit). H20 (0.8 L) was charged to the reaction flask and then agitated and the solids were filtered. H20 (4.0 L) was charged to the Buchner funnel, the slurry in the Buchner funnel was manually stirred with a spatula and allowed to soak for 10 minutes. Vacuum was reapplied to the Buchner funnel for 30 minutes. The solids were transferred into two trays, which were placed in a vacuum oven at 60 C with a nitrogen bleed for 18 hours. (4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5 -(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran2(3H)-one was isolated as a white crystalline solid (955.3 g, 2649 mmol, 96% yield). ?H NMR (400 MHz, Chloroform-cl) 4.50 (ddd, J= 6.7, 2.4, 2.4 Hz, 1H), 4.32 (m, 1H), 3.83 - 3.73 (m, 2H), 2.81 (dd, J= 17.6, 6.7 Hz, 1H), 2.38 (dd, J= 17.6, 2.6 Hz, 1H), 0.88 (s, 9H), 0.88 (s, 9H), 0.08 (s, 6H), 0.06 (s, 3H),0.06 (s, 3H).
80% With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 24.0h;Inert atmosphere; Imidazole (2.5 g, 37.3 mmol) and TBDMSCl (4.5 g, 29.8 mmol) were added to compound 17 (1.0 g, 7.57 mmol) dissolved in anhydrous DMF (20 mL). The mixture was stirred at ambient temperature for 1 day and quenched by the addition of water. The water layer was extracted with EtOAc (3 x 10 mL) and the organic layers were combined, washed with brine and dried with anhydrous Mg2SO4 and evaporated. The remaining residue was column chromatographed (90% hexane/EtOAc) to give 1814 (750 mg, 80%): 1H NMR (CDCl3) delta 0.08-0.10 (m, 12H), 0.80-0.91 (s, 18H), 2.35 (dd, J = 2.6, 17.6 Hz, 1H, H2), 2.80 (dd, J = 6.7, 17.6 Hz, 1H, H2'), 3.74 (dd, J = 2.5, 11.4 Hz, 1H, H5), 3.78 (dd, J = 3.2, 11.5 Hz, 1H, H5'), 4.30-4.32 (m, 1H, H3), 4.46-4.81 (m, 1H, H4).
61% With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 15℃; for 12.75h;Large scale; Example 46A (4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl) dihydrofuran-2(3H)-one To a solution of the product from Example 1A (1.95 kg, 14.7 mol), N,N-dimethylaminopyridine (90.1 g, 738 mmol) and imidazole (3.52 kg, 51.6 mol) in N,N-dimethylformamide (15.0 L) at 15 C. was added tert-butyldimethylsilyl chloride (5.34 kg, 35.4 mol) over ca. 45 min, and the mixture was stirred 12 hours. TLC (Petroleum ether:Ethyl acetate=20:1, Rf=0.40) indicated the starting material was consumed completely and one new spot formed. The reaction mixture was diluted with H2O (60 L) and extracted with methyl tert-butyl ether (10 L*3). The combined organic layers were washed with brine (3 L), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of 2-5% ethyl acetate in petroleum ether to give the title compound as a colorless solid (3.25 kg, 61% yield); 1H NMR (400 MHz, CDCl3) ??4.49 (dt, J=6.4, 2.0 Hz, 1H), 4.30-4.32 (m, 1H), 3.71-3.82 (m, 2H), 2.77-2.83 (m, 1H), 2.34-2.43 (m, 1H), 0.82-0.92 (m, 18H), 0.03-0.09 (m, 12H).
With triethylamine; In N-methyl-acetamide; hexane; water; 2-Deoxy-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-D-erythro-pentonoic Acid gamma-Lactone To a stirring solution, under argon, of 1.18 g of 2-deoxy-D-erythro-pentonoic acid gamma-lactone, prepared by the procedure described in carbohydrate Research, vol. 90, 1981, p 17-26, in 11 ml of dimethylformamide containing 3 ml of triethylamine is added dropwise a solution of 2.95 g of tert-butyldimethylsilyl chloride in 9 ml of dimethylformamide. The reaction mixture is stirred overnight at room temperature, poured into a mixture of 110 ml of hexane and 110 ml of water, the layers partitioned. The organic layer is washed with water, dried and concentrated to give 2.64 g of the desired product. mp 77-78 C. 1 H NMR(CDCl3): delta4.45(m,1H); 4.34(m,1H); 3.78(m,2H); 2.83(dd,1H); 2.38(d,1H); 0.9(s,18H).
With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 24.0h; EXAMPLE 3; [0153] 2-deoxy-3,5-di-0-(?-butyldimethylsilyl)-D-ribonolactone (7).; To a solution of 2- deoxy-D-ribose (1.0 g, 7.45 mmol) in 6 mL of water was added Br2 (2 mL). The flask was sealed and the content was stirred at room temperature for 5 days. The resulting mixture was neutralized by adding silver carbonate until the pH was 7. The mixture was filtered and the filtrate was concentrated under reduced pressure to yield 2-deoxyribonolactone as a yellow oil. Without further purification, the crude product was dissolved in 20 mL of anhydrous DMF, and imidazole (2.53 g, 37.3 mmol) and t-butyldimethylsilyl chloride (4.5 g, 29.8 mmol) were added. The resulting solution was stirred at room temperature for 24 h, and quenched by addition of water. Water layer was extracted by ethyl acetate (3x10 mL), organic layers were combined, washed with brine and dried over anhydrous Na2SO4. Crude product was concentrated in vacuo. Flash chromatography (hexanes:ethyl acetate 20:1) afforded 7 (3.2 g, 8.9 mmol, 89% yield after two steps) as white solid, mp = 72-73 0C. 1H NMR (CDCl3, 400 MHz), delta ppm: 0.038 (s, 3H), 0.051 (s, 3H), 0.062 (s, 6H), 0.085 (s, 18H)5 2.36 (dd, J= 2.6, 17.7 Hz, IH), 2.79 (dd, J= 6.7, 17.7 Hz, IH), 3.73 (dd, J= 2.5, 11.5 Hz, IH), 3.78 (dd, J= 3.4, 11.5 Hz, IH), 4.30 (dd, J= 2.5, 5.2 Hz, IH), 4.48 (dt, J= 2.3, 6.6 Hz, IH). 13C NMR (125 MHz, CDCl3), delta ppm: -5.7, -5.5, -4.9, -4.8, 17.9, 18.2, 25.7, 25.8, 39.0, 62.5, 69.6, 88.1, 175.8. HRMS (ESI): calcd. for CnH36O4Si2: 360.2152; Found: 360.2155.
With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; To a solution of 2 (150 mmol) in anhydrous DMF (2.5 mL/mmol) was added imidazole (750 mmol) followed by tert-butyldimethylsilyl chloride (600 mmol). The reaction mixture was stirred at room temperature overnight, then extracted with a mixture of ethyl acetate / saturated aqueous NaHCO3 solution. The reaction was monitored by TLC. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent: petroleum ether diethyl ether: 10%) to afford the expected compound as a white solid in 61% yield (2 steps). ?H NMR (CDC13, 400MHz) oe Qpm) 0.05-0.08 (m, 12H), 0.88 (s, 18H), 2.37 (dd, J 17.62 Hz and 2.57 Hz, 1H), 2.81 (dd, J= 17.62 Hz and 6.70 Hz, 1H), 3.75 (dd, J= 11.47Hz and 2.58 Hz, 1H), 3.80 (dd, J= 11.47 Hz and 3.26 Hz, 1H), 4.3 1-4.33 (m, 1H), 4.49 (dt, J 6.63 Hz and 2.35 Hz, 1H).

  • 2
  • [ 62325-30-8 ]
  • [ 83159-91-5 ]
  • [ 1132773-59-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,7-dibromophenanthrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: 3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone In tetrahydrofuran; hexane at -78℃; for 4.25h; Inert atmosphere; Further stages;
  • 3
  • [ 62325-30-8 ]
  • [ 83159-91-5 ]
  • [ 1132773-60-4 ]
  • [ 1132773-57-9 ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 1.5% Stage #1: 2,7-dibromophenanthrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: 3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone In tetrahydrofuran; hexane at -78℃; for 4.25h; Inert atmosphere; Stage #3: With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;
  • 4
  • [ 62325-30-8 ]
  • [ 83159-91-5 ]
  • [ 1132773-58-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,7-dibromophenanthrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: 3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone In tetrahydrofuran; hexane at -78℃; for 4.25h; Inert atmosphere; Further stages;
Same Skeleton Products
Historical Records