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[ CAS No. 7512-17-6 ] {[proInfo.proName]}

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Chemical Structure| 7512-17-6
Chemical Structure| 7512-17-6
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Product Details of [ 7512-17-6 ]

CAS No. :7512-17-6 MDL No. :MFCD00136044
Formula : C8H15NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :MBLBDJOUHNCFQT-LXGUWJNJSA-N
M.W : 221.21 Pubchem ID :1738118
Synonyms :
N-Acetyl-2-amino-2-deoxy-D-glucose;GlcNAc;NSC 400525;N-Acetylglucosamine;GreenNAG;Bio-NAG;Acetylglucosamine;NSC 524344;NAG;Marine Sweet

Calculated chemistry of [ 7512-17-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 7
Num. H-bond acceptors : 6.0
Num. H-bond donors : 5.0
Molar Refractivity : 48.42
TPSA : 127.09 Ų

Pharmacokinetics

GI absorption : Low
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) : -8.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : -2.07
Log Po/w (XLOGP3) : -1.72
Log Po/w (WLOGP) : -3.23
Log Po/w (MLOGP) : -2.73
Log Po/w (SILICOS-IT) : -1.4
Consensus Log Po/w : -2.23

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.33
Solubility : 477.0 mg/ml ; 2.16 mol/l
Class : Highly soluble
Log S (Ali) : -0.44
Solubility : 81.2 mg/ml ; 0.367 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 1.48
Solubility : 6620.0 mg/ml ; 29.9 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.14

Safety of [ 7512-17-6 ]

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 [ 7512-17-6 ]

* 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 [ 7512-17-6 ]
  • Downstream synthetic route of [ 7512-17-6 ]

[ 7512-17-6 ] Synthesis Path-Upstream   1~12

  • 1
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  • [ 470-69-9 ]
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YieldReaction ConditionsOperation in experiment
22.1% With Aspergillus oryzae NBRC100959 mycelia In citrate buffer at 30℃; for 8 h; Enzymatic reaction The hydrolytic activity of β-fructofuranosidase was assayed using sucrose as a substrate, and was monitored by measuring the amount of reducing sugar released from sucrose. The enzyme solution (50 μL) was added to 50 μL of 0.4percent sucrose in 20 mM Na citrate buffer (pH 5.5) and the mixture was incubated at 30 °C. After incubation, the enzymatic reaction was stopped by heating the sample at 95 °C for 5 min. The amount of reducing sugar in the reaction mixture was determined by the Somogyi-Nelson method using glucose as a standard.22 One unit (U) of enzyme activity was defined as the amount of enzyme required to hydrolyze 1 μmol of sucrose per minute under the assay conditions.
Reference: [1] Carbohydrate Research, 2012, vol. 353, p. 27 - 32
  • 2
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  • [ 13343-62-9 ]
YieldReaction ConditionsOperation in experiment
74% With hydrogenchloride In water at 90℃; for 3 h; Inert atmosphere To a solution of N-acetylglucosamine (6.40 g, 28.9 mmol)in benzyl alcohol (50 mL, 480 mmol), concd aq HCl (3.0 mL) wasadded and the reaction mixture was stirred at 90 C for 3 h. Thecrude mixture was cooled down to rt, poured into Et2O (500 mL)and left to crystallize at 4 C for 18 h. The crystalline product wasfiltered and washed with petroleum ether. Purification by silica gelcolumn chromatography (CH2Cl2/MeOH, 95:5/88:12, v/v) gavebenzyl glycoside 2 (6.67 g, 21.4 mmol, 74percent) as a white foam.Rf0.25 (CH2Cl2/MeOH, 90:10, v/v); mp 182e184 C; [a]D17.8 222(c 0.1, MeOH); IR (film) 3298, 3092, 2938, 2901, 2844, 1648, 1552,1497, 1455, 1375, 1309, 1230, 1156, 1093, 1047, 778, 732, 695 cm1;1H NMR (500 MHz, CD3OD) d 7.40e7.25 (m, 5H, CHarom), 4.85 (d,1H, J10,203.6 Hz, H-10), 4.74 (d, 1H, J1a,1b12.0 Hz, H-1a), 4.49 (d,1H, J1a,1b12.0 Hz, H-1b), 3.89 (dd, 1H, J10,203.6 Hz, J20,3010.8 Hz,H-20), 3.83 (dd, 1H, J50,6a01.6 Hz, J6a0,6b011.4 Hz, H-6a0), 3.73e3.64(m, 3H, H-6b0, H-30, H-40), 3.36 (dd, 1H, J40,50J50,6b09.6 Hz, H-50),1.95 (s, 3H, CH3 Ac); 13C NMR (125 MHz, CD3OD) d 173.6 (C]O Ac),139.0 (Cqarom), 129.4 (C-oarom), 129.3 (C-marom), 128.8 (C-parom),97.5 (C-10), 74.1 (C-40), 72.7 (C-30), 72.5 (C-50), 70.1 (C-1), 62.7 (C-60), 55.4 (C-20), 22.5 (CH3 Ac); HRMS(ESI) m/z calcd for[C15H22NO6]: 312.1442, obsd: 312.1446.
72% With toluene-4-sulfonic acid In toluene at 130℃; for 4 h; Dean-Stark N-acetylglucosamine (1) (10 g, 0.045 mol) and benzylalcohol (72 mL) were suspended in toluene (120 mL)and p-toluene sulfonic acid monohydrate (500 mg) wasadded. The reaction mixture was refluxed (130 °C) in aDean-Stark apparatus with water removal by azeotropicmixture. After 4 h, the reaction mixture was cooled toambient temperature and saturated solution of sodiumhydrogen carbonate was added to pH ~ 6. Toluene wasremoved under reduced pressure. Residue was split intoether-hexane (vol. ratio = 2:1, 260 mL) mixture. Reactionmixture was vigorously stirred for 3h and left overnightin refrigerator. The amorphous precipitate wasfiltered off, washed with ether and the crude product recrystallizedfrom 2-propanol to yield colourless crystals2 (10.1 g, 72percent yield). Rf (A) = 0.42; m.p. 186–187 °C(lit. 185–186 °C)20; [α]D = +170 ° c 1, water (lit. [α]D =+168 ° c 1, water)20; 1H NMR (DMSO-d6) δ/ppm: 7.81(d, 1H, J = 8.2 Hz, NH), 7.35–7.28 (m, 5H, Ph), 5.01 (d,1H, J = 5.8 Hz, OH-4), 4.73 (d, 1H, J = 5.8 Hz, OH-3),4.70 (d, 1H, J = 3.2 Hz, H-1), 4.66 (d, 1H, J = 12.3 Hz,CH2b-Ph), 4.54 (t, 1H, J = 5.8 Hz, OH-6), 4.41 (d, 1H,J = 12.3 Hz, CH2a-Ph), 3.68 (m, 1H, H-2), 3.65 (m, 1H,H-6b), 3.53 (m, 1H, H-3), 3.50 (m, 1H, H-6a), 3.45 (m,1H, H-5), 3.16 (m, 1H, H-4), 1.83 (s, 3H, CH3-CON acetyl); 13C NMR (DMSO-d6) δ/ppm: 169.4 (CO acetyl),137.9 (Ph (C)), 128.1–127.4 (Ph(CH)), 95.9 (C-1),73.1 (C-5), 70.9 (C-4), 70.6 (C-3), 67.7 (CH2-Ph), 60.8(C-6), 53.7 (C-2), 22.5 (CH3-CON acetyl); MS-ESI m/z312 [M+H]+.
71% With hydrogenchloride In water at 90℃; for 3 h; Inert atmosphere N-Acetyl glucosamine 7 (6.00 g, 27.1 mmol) was dissolved in benzyl alcohol(50 mL) and concentrated HCl (2.9 mL) was added. The mixture was heatedto 90C for 3 h, cooled to rt, and then poured onto 500 mL Et2O and storedovernight at −20C. The resulting precipitate was recovered by filtration andrinsed with Et2O and hexanes to yield 17.64 g of crude material, which waspurified by silica gel chromatography (8percent to 15percent MeOH/CH2Cl2) to provide11 (5.98 g, 71percent) as white foam. Comparison of 1H NMR with literature valuesconfirmed the identity of compound 11.[28] 1H NMR (500 MHz, CD3OD), δ 1.95(s, 3H, COCH3), 3.37–3.39 (m, 1H), 3.69–3.73 (m, 3H), 3.82 (d, 1H, J3 = 9.5 Hz),3.89 (dd, 1H, J3 = 3.5, 11 Hz), 4.49 (d, 1H, J3 = 12 Hz), 4.74 (d, 1H, J3 =11.5 Hz), 7.28–7.40 (m, 5H, aromatic).
27% at 80℃; for 3.5 h; A mixture of 2-acetamido-2-deoxy-D-glucopyranose [Compound Ij (15.0 g, 0.068 mol), Amberlite JR 120 [Hj ion exchange resin (15.0 g) in benzyl alcohol (125 mL) was stirred at 80°C for 3.5 hours. The reaction mixture was filtered. The filtrate was evaporated under reduced pressure at 90°C. The residue was taken up in hot isopropanol (60 mL) and filtered. The filtrate was left to crystallize, thewhite crystalline solid was filtered off, washed twice with cold isopropanol (20 mL) and twice with ether (200mL) to give benzyl 2-acetamido-2-deoxy-D- glucopyranoside [Compound JJj (5.62 g, yield 27percent).
15%
Stage #1: With boron trifluoride diethyl etherate In acetonitrile at 20℃;
Stage #2: With bacterial β-N-acetyl-hexosaminidase from Zobellia galactanivorans In aq. phosphate buffer at 37℃; for 24 h; Enzymatic reaction
General procedure: The purified α/β mixtures 2a/3a, 2b/3b, 2c/3c, 2d/3d, or 2e/3e were dissolved inNa3PO4/citratebuffer (50mM, pH8.0) and0.1UofZgβHexN2854 hexosaminidasewere added (final volume 5 mL). The reaction mixture was incubated at 37 ° for12 h in the case of 2a/3a, 2b/3b, 2c/3c, and2d/3d and 24 h in the case of 2e/3e. Then,the solvent was evaporated under reduced pressure. The residue was subjected tosilica-gel column chromatography. 2a, 2b, 2c, 2d, and 2e were obtained as whitesolids by eluting them with an AcOEt/MeOH 9:1 mixture (Yields: 2a: 32percent, 2b: 53percent,2c: 44percent, 2d: 9percent, 2e: 15percent).

Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3515 - 3517
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 238 - 242
[3] Chemistry - A European Journal, 2016, vol. 22, # 49, p. 17813 - 17819
[4] Journal of the American Chemical Society, 2012, vol. 134, # 22, p. 9343 - 9351
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 11, p. 1853 - 1856
[6] Carbohydrate Research, 2015, vol. 414, p. 1 - 7
[7] Croatica Chemica Acta, 2015, vol. 88, # 2, p. 151 - 157
[8] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1269 - 1275
[9] Journal of Carbohydrate Chemistry, 2013, vol. 32, # 5-6, p. 392 - 409
[10] Collection of Czechoslovak Chemical Communications, 2005, vol. 70, # 10, p. 1615 - 1641
[11] Journal of Medicinal Chemistry, 2016, vol. 59, # 14, p. 6878 - 6890
[12] Synthetic Communications, 2008, vol. 38, # 18, p. 3052 - 3061
[13] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 9, p. 628 - 634
[14] Arkivoc, 2012, vol. 2012, # 6, p. 90 - 100
[15] Journal of Medicinal Chemistry, 2007, vol. 50, # 2, p. 364 - 373
[16] Journal of the American Chemical Society, 2014, vol. 136, # 35, p. 12283 - 12295
[17] Patent: WO2017/98529, 2017, A1, . Location in patent: Page/Page column 18; 34
[18] Journal of Carbohydrate Chemistry, 2016, vol. 35, # 8-9, p. 423 - 434
[19] Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8137 - 8145
[20] Carbohydrate Research, 1980, vol. 82, p. 71 - 84
[21] Tetrahedron Asymmetry, 2010, vol. 21, # 15, p. 1936 - 1941
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Reference: [1] Organic Letters, 2011, vol. 13, # 19, p. 5306 - 5309
[2] Liebigs Annalen der Chemie, 1991, # 12, p. 1291 - 1300
[3] Justus Liebigs Annalen der Chemie, 1958, vol. 611, p. 236,239
[4] Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 11, p. 2989 - 2995
[5] Organic and Biomolecular Chemistry, 2009, vol. 7, # 6, p. 1203 - 1210
  • 4
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  • [ 3055-51-4 ]
  • [ 13343-62-9 ]
YieldReaction ConditionsOperation in experiment
26 % de With boron trifluoride diethyl etherate In acetonitrile at 20℃; General procedure: To a solution of 1 (100 mg, 0.45 mmol) in acetonitrile (15 mL) and the correspondingalcohol (20mmol, methanol (a), ethanol (b), 2-propanol (c), n-butanol (d), orbenzyl alcohol (e)), boron trifluoride diethyl etherate (300μL, 2.3mmol) was added.The reaction mixture was stirred at room temperature overnight. Then, the solventwas evaporated under reduced pressure. The residue was then subjected to silica-gelcolumn chromatography. The α/β mixture of the N-acetyl-D-glucosamine derivativewas obtained as a white solid by eluting the compound with an AcOEt/MeOH9:1 mixture (2a/3a 51:49 mixture: 74percent yield, 2b/3b 80:20 mixture: 68percent yield, 2c/3c82:18 mixture: 58percent yield, 2d/3d 87:13 mixture: 18percent yield, 2e/3e 63:37 mixture: 25percentyield).
Reference: [1] Liebigs Annalen der Chemie, 1986, vol. 1986, # 1, p. 37 - 45
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 18, p. 5807 - 5812
[3] Carbohydrate Research, 2011, vol. 346, # 14, p. 2294 - 2299
[4] Glycoconjugate Journal, 2010, vol. 27, # 5, p. 549 - 559
[5] Journal of Carbohydrate Chemistry, 2016, vol. 35, # 8-9, p. 423 - 434
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  • [ 100-39-0 ]
  • [ 3055-51-4 ]
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Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 43, p. 7567 - 7570
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3181 - 3193
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Reference: [1] Patent: US2004/58888, 2004, A1,
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Reference: [1] ACS Chemical Biology, 2017, vol. 12, # 8, p. 2216 - 2224
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  • [ 3068-32-4 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 14, p. 3019 - 3026
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  • [ 57-60-3 ]
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Reference: [1] Bioscience, Biotechnology and Biochemistry, 2005, vol. 69, # 10, p. 1944 - 1950
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Reference: [1] Bioscience, Biotechnology and Biochemistry, 2005, vol. 69, # 10, p. 1944 - 1950
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Reference: [1] Biochemical Journal, 1958, vol. 68, p. 57,59
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  • [ 66-84-2 ]
Reference: [1] Patent: US9267141, 2016, B2, . Location in patent: Page/Page column 14
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