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[ CAS No. 1174157-65-3 ] {[proInfo.proName]}

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Chemical Structure| 1174157-65-3
Chemical Structure| 1174157-65-3
Structure of 1174157-65-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1174157-65-3 ]

CAS No. :1174157-65-3 MDL No. :MFCD13184973
Formula : C10H11NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :WKIKHHMUNOVQLD-UHFFFAOYSA-N
M.W : 225.20 Pubchem ID :51340986
Synonyms :

Calculated chemistry of [ 1174157-65-3 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.81
TPSA : 72.91 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) : -8.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : -0.87
Log Po/w (WLOGP) : -0.67
Log Po/w (MLOGP) : 0.14
Log Po/w (SILICOS-IT) : 0.69
Consensus Log Po/w : 0.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.29
Solubility : 115.0 mg/ml ; 0.51 mol/l
Class : Very soluble
Log S (Ali) : -0.18
Solubility : 149.0 mg/ml ; 0.661 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.84
Solubility : 32.7 mg/ml ; 0.145 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.76

Safety of [ 1174157-65-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1174157-65-3 ]

* 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 [ 1174157-65-3 ]

[ 1174157-65-3 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 1174157-65-3 ]
  • [ 1610762-73-6 ]
  • [ 955094-26-5 ]
  • [ 1610762-75-8 ]
YieldReaction ConditionsOperation in experiment
35% With triethylamine In N,N-dimethyl-formamide at 20℃;
  • 2
  • [ 1174157-65-3 ]
  • TMV<SUB>Lys</SUB> mutant (TMV - rod-shaped tobacco mosaic virus) [ No CAS ]
  • TMV<SUB>Lys</SUB> mutant (TMV - rod-shaped tobacco mosaic virus) with exterior lysine residues (Lis158) targeted with propargyl-NHS ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer; dimethyl sulfoxide
  • 3
  • [ 1174157-65-3 ]
  • [ 25316-40-9 ]
  • C33H35NO13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;
  • 4
  • [ 1174157-65-3 ]
  • C52H69N17O9 [ No CAS ]
  • C58H75N17O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; A general procedure for post-synthetic terminal functionalization of polyamides by azide or alkyne moieties 11-14 General procedure: The activated ester of appropriate acid 4, 8, 9 or 10 (94 μmol, 10 equiv) was added to polyamide (10 mg, 9.4 μmol, 1 equiv), dissolved in 200 μL of DMF and 80 μL of N-ethyldiisopropylamine (470 μmol, 50 equiv). After incubation for 2 h at room temperature, the reaction mixture was precipitated by ether. The analysis of the precipitate by RP-HPLC and TLC showed completion of the reaction. The product was purified by semi-preparative HPLC on a C-18 X-Terra (7μm) column (7,7 × 300 mm; Waters), using a linear gradient of 0-80% MeCN in H2O containing 0.1% of TFA at a flow rate of 2 mL/min. After solvent removal, the product (11-14) was dried in vacuo. Yields were 50 %, for 11, ES-Q-TOF-MS: 1228.24 ([M-H]-; calc. 1228.63); 17% for 12, ES-Q-TOF-MS: 1215.3 ([M-H]-; calc. 1215.62); 83 % for 13, ES-Q-TOF-MS: 1186.17 ([M-H]-; calc. 1186.32); 39 % for 14, ES-Q-TOF-MS: 1349.13 ([M-H]-; calc. 1349.68)
  • 5
  • [ 1174157-65-3 ]
  • endomorphin 1 [ No CAS ]
  • C40H44N6O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine In dimethyl sulfoxide; N,N-dimethyl-formamide at 4℃;
  • 6
  • [ 1174157-65-3 ]
  • C42H48FN9O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide; dimethyl sulfoxide / 4 °C 2: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water / 20 °C
  • 7
  • [ 1174157-65-3 ]
  • C43H50FN9O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide; dimethyl sulfoxide / 4 °C 2: copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 20 °C
  • 8
  • [ 1174157-65-3 ]
  • C43H50FN9O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide; dimethyl sulfoxide / 4 °C 2: copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 20 °C
  • 9
  • [ 1174157-65-3 ]
  • C42H48(18)FN9O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide; dimethyl sulfoxide / 4 °C 2: copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 0.17 h / 20 °C
  • 10
  • 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine [ No CAS ]
  • [ 1174157-65-3 ]
  • (R)-2,3-bis(palmitoyloxy)propyl-2-(3-(prop-2-ynyloxy)propaneamido)ethyl phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydrogencarbonate In methanol; chloroform; water at 20℃; for 6h; 1.A Reference Example 1. A.: Synthesis of DPPEP [compound of formula (1)] 500 mg of 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (hereinafter: DPPE, 0.72 mmol) was mixed in 10 ml of chloroform/methanol 65:35 (v/v) mixture. To this was added 250 mg of 3-(prop-2-ynyloxy)propanoic acid succinimidyl ester (hereinafter: propargyl-NHS, 1.11 mmol) dissolved in 2.5 ml of chloroform/methanol 65:35 (v/v) mixture. While stirring at room temperature, further 1000 i.il of 8.4% NaHCO3 aqueous solution was added to the reaction mixture. After stirring briefly the solution cleared up, and a homogeneous solution was obtained. Stirring was continued for 6 hours at room temperature and the solvent was evaporated nearly to dryness under reduced pressure at40°C. To the oily yellowish-white residue 20 ml of 0.5 M hydrochloric acid solution and 50 ml of diethyl ether were added. After mild stirring, the oily residue dissolved, both phases remained clear. After separation the ether phase was extracted with additional 3 x 20 ml of 0.5 M hydrochloric acid. The ether phase was then dried over sodium sulphate, was filtered, and was evaporated to dryness at 35°C under reduced pressure. The white fluffy product thus obtained (521 mg, 93% DPPEP) provedto be sufficiently pure based on HPLC-MS analysis. For assessing the purity of DPPEP, Alltima HP C-18-Amide-3 im (150x2.1 mm) column was used. Theflow rate of the mobile phase was 1 mI/mm, while its composition was A: 10 mM NH4OAc (pH 9.5), B:Acetonitrile, from 85% (B) to 98% (B) with linear gradient elution over 8 minutes. The elution time ofDPPEP was between 4 and 4.5 minutes under these conditions. The 1H and 13C NMR measurement of DPPEP confirmed the structure of the molecule: 1H NMR(CDCI3), dlH(ppm): 0.88 (6H, t, J = 6.7 Hz); 1.27 (48H, m); 1.60 (4H, m); 2.31 (2H, t, J = 7.6 Hz); 2.33(2H, t, J = 7.6 Hz); 2.49 (1H, t, J = 2.6 Hz); 2.55 (2H, t, J = 6.4 Hz); 3.54 (2H, t, J = 5.0 Hz); 3.82 (2H, t, J =6.4 Hz); 4.05 - 4.20 (7H, m); 4.35 (1H, dd, J = 12.0, 4.1 Hz); 5.24 (1H, m); 6.13 (2H, br.s); 7.02 (1H,br.s). 13C NMR (CDCI3), di3c(ppm): 14.1; 22.7; 24.8; 29.0; 29.1; 29.3; 29.5; 29.6; 29.7; 31.9; 34.0; 34.2;36.4; 39.8 (d, 3Jcp= 6.5 Hz); 58.3; 61.9; 65.1 (d, 2Jcp= 5.6 Hz); 65.8; 66.3 (d, 2Jcp= 5.9 Hz); 69.4 (d, 3Jcp = 7.5 Hz); 75.0; 79.2; 172.2; 173.1; 173.4.
  • 11
  • [ 1174157-65-3 ]
  • C43H49N5O17S [ No CAS ]
  • C49H55N5O19S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3h; 40 Example 40 Compound 75 (3 eq), purchased from Click Chemistry Tools (CAS: 1174157- 65-3), was dissolved in DMF and DIPEA, and added to compound 57. The reaction was stirred for 3 h until completion as monitored by LC-MS. The reaction mixture was neutralized with acetic acid and directly purified by preparative HPLC to yield compound 62. LC-MS (Method A): = 1.43 min, MS (m/z.) calculated 1050.06 (M+H)+, found 1050.07.
  • 12
  • [ 1174157-65-3 ]
  • C43H49N5O17S [ No CAS ]
  • C49H55N5O19S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 41 Example 41 Compound 75 (3 eq), purchased from Click Chemistry Tools (CAS: 1174157- 65-3), was dissolved in DMF and DIPEA, and added to compound 57. The reaction was stirred for 3 h until completion as monitored by LC-MS. The reaction mixture was neutralized with acetic acid and directly purified by preparative HPLC to yield compound 62.
  • 13
  • [ 1174157-65-3 ]
  • C35H50N2O14Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h
  • 14
  • [ 1174157-65-3 ]
  • C29H36N2O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3: acetic acid / tetrahydrofuran; water / 24 h / 20 °C
  • 15
  • [ 1174157-65-3 ]
  • C32H37N5O15 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 4: dichloromethane / 0.5 h
  • 16
  • [ 1174157-65-3 ]
  • C30H38N2O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 4: dichloromethane / 0.5 h 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h
  • 17
  • [ 1174157-65-3 ]
  • C54H56FN5O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 4: dichloromethane / 0.5 h 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 60 °C
  • 18
  • [ 1174157-65-3 ]
  • C47H48FN5O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3.1: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 4.1: dichloromethane / 0.5 h 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 60 °C 6.1: lithium hydroxide / methanol / 0.08 h / Sonication 6.2: 0.08 h
  • 19
  • [ 1174157-65-3 ]
  • C50H59N3O21S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3.1: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 4.1: dichloromethane / 0.5 h 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h 6.1: chloro-trimethyl-silane / dichloromethane / 0.33 h 6.2: 1 h
  • 20
  • [ 1174157-65-3 ]
  • C28H41N3O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3.1: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 4.1: dichloromethane / 0.5 h 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h 6.1: chloro-trimethyl-silane / dichloromethane / 0.33 h 6.2: 1 h 7.1: lithium hydroxide / tetrahydrofuran; methanol; water / 1 h / 0 - 20 °C
  • 21
  • [ 1174157-65-3 ]
  • C50H57N5O22S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.75 h 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h 3.1: acetic acid / tetrahydrofuran; water / 24 h / 20 °C 4.1: dichloromethane / 0.5 h 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h 6.1: chloro-trimethyl-silane / dichloromethane / 0.33 h 6.2: 1 h 7.1: lithium hydroxide / tetrahydrofuran; methanol; water / 1 h / 0 - 20 °C 8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
  • 22
  • [ 107-97-1 ]
  • [ 1174157-65-3 ]
  • C9H13NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.75h; 50 Example 50 Compound 75 (1.05 g, 4.66 mmol), referred to as PropargOPr and obtained from Click Chemistry Tools (CAS: 1174157-65-3), was dissolved in DMF (10 mL). H- Sar-OH (831 mg, 9.33 mmol), which is N-methyl glycine, and DIPEA (2.4 mL, 14 mmol) were added. The reaction was stirred for 45 minutes, quenched AcOH, and purified by prep-HPLC. Fractions containing the desired product were concentrated to afford compound 76 as a colorless solid (821.3 mg, 4.12 mmol, 88%). LC-MS (Method A): tR = 0.81 min; MS (m/z) [M + H]+ calc for C9H14NO4 200.09, found 199.72.
  • 23
  • [ 1174157-65-3 ]
  • 1-ammine-undecahydrododecaborate [ No CAS ]
  • C6H19B12NO2(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile
  • 24
  • [ 1174157-65-3 ]
  • C38H54N6O11S [ No CAS ]
  • C50H66N6O15S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C38H54N6O11S With triethylamine In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: 2,5-dioxopyrrolidin-1-yl 3-(prop-2-ynyloxy)propanoate In dimethyl sulfoxide 2 NH2-Lys(NH2)-PEG4-sulfo-DBCO (37 mg, 0.046 mmol, 1 eq) was dissolved in 1 mL of DMSO before TEA (19.3 uL, 0.14 mmol, 3 eq) was added. After stirring for 5 minutes at room temperature, propargyl NHS ester (22.8 mg, 0.1 mmol, 2.2 eq) was added to the reaction flask. After 1 hr the reaction was complete and confirmed by LC-MS. The product, sulfo-DBCO-PEG4-Pg2 was used without further purification. ESI-MS: m/z = 1023.4 (M-H)+.
  • 25
  • [ 1025796-31-9 ]
  • [ 1174157-65-3 ]
  • (3S,7S)-tri-tert-butyl 5,13-dioxo-16-oxa-4,6,12-triazanonadec-18-yne-1,3,7-tricarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
  • 26
  • [ 1174157-65-3 ]
  • preQ1-C6-NH<SUB>2</SUB> [ No CAS ]
  • C19H28N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
91% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Scheme 3. Synthesis of the preQ1-alkyne To the solution of alkyne-NHS ester (30.0 mg, 0.13 mmol, commercially available from BroadPharm, San Diego, USA; CAS: 1174157-65-3) in DMF (3 mL) was added previously reported preQ1-C6-NH2(41.9 mg, 0.13 mmol) and DIEA (38.7 mg, 0.30 mmol). The resulting solution was stirred overnight. After the substitution reaction completed, the solution was directly dried in vacuo. Then the mixture was purified by flash chromatography (0-50% EtOAc in hexanes) to afford the product preQ1-alkyne as pale white solid (45.9 mg, 91%).1H NMR (500 MHz, Methanol-d4) δ 6.87 (s, 1H), 4.28 (s, 2H), 4.17 (d, J = 2.4 Hz, 2H), 3.79 (t, J = 6.1 Hz, 2H), 3.38 (s, 1H), 3.24 - 3.18 (m, 2H), 3.08 (t, J = 7.5 Hz, 2H), 2.89 (t, J = 2.4 Hz, 1H), 2.46 (t, J = 6.1 Hz, 2H), 1.76 (p, J = 7.5 Hz, 2H), 1.56 (p, J = 7.1 Hz, 2H), 1.51 - 1.36 (m, 4H). 13C NMR (126 MHz, Methanol-d4, δ): δ 172.09, 161.06, 152.92, 152.39, 117.49, 108.24, 98.06, 78.87, 74.52, 74.25, 65.43, 57.27, 45.99, 43.22, 38.44, 35.92, 28.48, 25.67, 15.71. HRMS (M+H+) calcd for [C19H29N6O3]+ 389.2298, found 389.2296.
  • 27
  • [ 1174157-65-3 ]
  • preQ1-C6-NH<SUB>2</SUB> [ No CAS ]
  • preQ1-DEACM-preQ1 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: copper(II) bromide; 1-(1-benzyltriazol-4-yl)-N,N-bis[(1-benzyltriazol-4-yl)methyl]methanamine / lithium hydroxide monohydrate; dimethyl sulfoxide / 2 h / Darkness
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide 2: copper(II) bromide / lithium hydroxide monohydrate; dimethyl sulfoxide / 2 h / Darkness
  • 28
  • [ 1174157-65-3 ]
  • C38H54N6O11S [ No CAS ]
  • C50H66N6O15S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C38H54N6O11S With triethylamine In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: 2,5-dioxopyrrolidin-1-yl 3-(prop-2-ynyloxy)propanoate In dimethyl sulfoxide for 1h; 2 NH2-Lys(NH2)-PEG4-sulfo-DBCO (37 mg, 0.046 mmol, 1 eq) was dissolved in 1 mL of DMSO before TEA (19.3 µL, 0.14 mmol, 3 eq) was added. After stirring for 5 minutes at room temperature, propargyl NHS ester (22.8 mg, 0.1 mmol, 2.2 eq) was added to the reaction flask. After 1 h the reaction was complete and confirmed by LC-MS. The product, sulfo-DBCO-PEG4- Pg2 was used without further purification. ESI-MS: m/z = 1023.4 (M+H)+
  • 29
  • [ 1174157-65-3 ]
  • [ 32677-01-3 ]
  • C11H15NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 20℃; for 1h; 4 [00888] To compound 1 (200 mg, 0.676 mmol) in DCM (4 mL) was added TEA (218 uL, 1.56 mmol) then compound 2 (198 mg, 0.879 mmol) and the mixture was stirred at room temperature for 1 hour. Upon completion all volatiles were removed and crude compound 3 was deprotected using 4N HCl and was used subsequently without further purification.
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 20 °C 2: hydrogenchloride / lithium hydroxide monohydrate
  • 30
  • [ 1174157-65-3 ]
  • [ 32677-01-3 ]
  • C19H31NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 20℃; for 1h; Synthesis of LP106-p To compound 1 (200 mg, 0.676 mmol) in DCM (4 mL) was added TEA (218 uL, 1.56 mmol) then compound 2 (198 mg, 0.879 mmol) and the mixture was stirred at room temperature for 1 hour. Upon completion all volatiles were removed and crude compound 3 was deprotected using 4N HCI to provide acid 5 which was used subsequently without further purification.
With triethylamine In dichloromethane at 20℃; for 1h; Synthesis of LP106-p To compound 1 (200 mg, 0.676 mmol) in DCM (4 mL) was added TEA (218 uL, 1.56 mmol) then compound 2 (198 mg, 0.879 mmol) and the mixture was stirred at room temperature for 1 hour. Upon completion all volatiles were removed and crude compound 3 was deprotected using 4N HCl to provide acid 5 which was used subsequently without further purification.
  • 31
  • [ 1174157-65-3 ]
  • [ 32677-01-3 ]
  • C15H23NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 20 °C 2: hydrogenchloride
  • 32
  • [ 1174157-65-3 ]
  • 3-aminopropyl (2-acetamido-2-deoxy-α-L-altropyranosyluronic acid)-(1→3)-(2-acetamido-4-amino-2,4,6-trideoxy-β-D-galactopyranosyl)-(1→4)-(2-acetamido-2-deoxy-α-L-altropyranosyluronic acid)-(1→3)-2-acetamido-4-amino-2,4,6-trideoxy-β-D-galactopyranoside [ No CAS ]
  • C41H65N7O21 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 0.5h; 25 Tetrasaccharide 65b (1.1 mg, 1.25 μmol, 1.0 equiv.) was dissolved in 0.1 M phosphate buffer pH 7.8 (300 μL) and stirred vigorously at rt. A solution of propargyl-N-hydroxysuccinimidyl ester (393 μg, 15 μmol, 1.4 equiv.) in DMSO (50 μL) was added. After stirring for 30 min at rt, RP-HPLC monitoring indicated full consumption. The total volume was purified by RP-HPLC. Amide 99b (0.9 mg, 73%) was obtained as a white lyophilized powder. The linker-equipped tetrasaccharide 99b had RP-HPLC (215 nm / ELSD): Rt = 9.0 / 9.1 min (conditions D). HRMS (ESI+): m/z [M+H]+ calcd for C41H66N7O21S 992.4306, found 992.4307
  • 33
  • [ 1174157-65-3 ]
  • C15H31N2O13P*C6H15N [ No CAS ]
  • C21H36N2O15P(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With sodium salt of phosphorous acid; sodium chloride Inert atmosphere;
  • 34
  • [ 1174157-65-3 ]
  • (2S,4R)-2-amino-4-(4-((4-((E)-(4-((2-azidoethyl)(ethyl)amino)phenyl)diazenyl)phenyl)amino)-4-oxobutyl)pentanedioic acid [ No CAS ]
  • C35H43N9O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper oxide (I); L-ascorbic acid In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 0.75h; Inert atmosphere;
Same Skeleton Products
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