[ CAS No. 66640-86-6 ] {[proInfo.proName]}

Name: 66640-86-6|5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanehydrazide|95%
Brand: Ambeed
SKU: A126955
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Quality Control of [ 66640-86-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 66640-86-6 ]

SDS Specification

Alternatived Products of [ 66640-86-6 ]

Product Details of [ 66640-86-6 ]

CAS No. :	66640-86-6	MDL No. :	MFCD00078532
Formula :	C₁₀H₁₈N₄O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KOZWHQPRAOJMBN-ZKWXMUAHSA-N
M.W :	258.34	Pubchem ID :	83872
Synonyms :		Chemical Name :	5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanehydrazide

Calculated chemistry of [ 66640-86-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	6
Num. H-bond acceptors :	3.0
Num. H-bond donors :	4.0
Molar Refractivity :	73.28
TPSA :	121.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.98
Log Po/w (XLOGP3) :	-0.66
Log Po/w (WLOGP) :	-1.06
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	-0.34
Consensus Log Po/w :	-0.15

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.63
Solubility :	60.6 mg/ml ; 0.234 mol/l
Class :	Very soluble
Log S (Ali) :	-1.42
Solubility :	9.85 mg/ml ; 0.0381 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.94
Solubility :	2.99 mg/ml ; 0.0116 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.59

Safety of [ 66640-86-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 66640-86-6 ]

* 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 [ 66640-86-6 ]
Downstream synthetic route of [ 66640-86-6 ]

[ 66640-86-6 ] Synthesis Path-Upstream 1~3

1
[ 91853-90-6 ]
[ 66640-86-6 ]

Reference： [1] Bioconjugate Chemistry, 2010, vol. 21, # 5, p. 979 - 987
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 19, p. 4689 - 4693

2
[ 608-16-2 ]
[ 66640-86-6 ]

Reference： [1] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18140 - 18148
[2] Journal of Biological Chemistry, 1942, vol. 144, p. 513,516

3
[ 58-85-5 ]
[ 66640-86-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 19, p. 4689 - 4693
[2] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18140 - 18148

[ 66640-86-6 ] Synthesis Path-Downstream 1~54

1
[ 608-16-2 ]
[ 66640-86-6 ]

Yield	Reaction Conditions	Operation in experiment
296.0 mg	With hydrazine; In methanol; at 20℃; for 17h;	To a suspension of biotin (300 mg, 1.23 mmol) in MeOH (3 mL) was addedSOCl2 (0.30 mL, 4.0 mmol), and the solution was stirred overnight at roomtemperature to give a clear solution. After evaporation of the solvent and excessSOCl2 under reduced pressure, biotin methyl ester was obtained. The biotin methyl ester was used without further purification. Biotin methyl ester was dispersed inMeOH (3 mL), and hydrazine (0.175 mL, 2.92 mmol) was added with stirring. Afterstirring for 17 h, the solution was concentrated under reduced pressure and dilutedwith water (50 mL). The aqueous layer was washed by CH2Cl2 (30 mL × 3), andconcentrated in vacuo to give Biotinylhydrazine. Biotinylhydrazine was obtained as awhite solid powder (296.0 mg, about 100percent).

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 18140 - 18148
[2]Journal of Biological Chemistry,1942,vol. 144,p. 513,516
[3]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 707 - 712

2
[ 1121-60-4 ]
[ 66640-86-6 ]
5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid [1-pyridin-2-yl-meth-(E)-ylidene]-hydrazide [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. S147-S149

3
[ 66640-86-6 ]
[ 10111-08-7 ]
5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid [1-(1H-imidazol-2-yl)-meth-(E)-ylidene]-hydrazide [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. S147-S149

4
[ 66640-86-6 ]
2,2-bis(1H-pyrazol-1-yl)acetic acid [ No CAS ]
5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid N'-(2,2-di-pyrazol-1-yl-acetyl)-hydrazide [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. S147-S149

5
[ 66640-86-6 ]
gramicidin A [ No CAS ]
biotin-tagged gramicidin A [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 1563 - 1565

6
[ 66640-86-6 ]
alamethicin [ No CAS ]
biotin-tagged alamethicin [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 1563 - 1565

7
[ 66640-86-6 ]
poly[3-(N-succinimido-p-phenylcarboxylate(tetraethoxy)oxy)-4-methylthiophene]-2,5-diyl}; monomer(s): 3-(N-succinimido-p-phenylcarboxylate(tetraethoxy)oxy)-4-methylthiophene [ No CAS ]
poly[3-(p-phenyl(carbonylhydrazonobiotin)(tetraethoxy)oxy)-4-methylthiophene]-2,5-diyl}; monomer(s): 3-(N-succinimido-p-phenylcarboxylate(tetraethoxy)oxy)-4-methylthiophene; biotin hydrazine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 12463 - 12468

8
[ 66640-86-6 ]
CH₃C(O)-Aib-Pro-Aib-Ala-Aib-Ala-Gln(Trt)-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu(O-t-Bu)-Gln(Trt)-Phe-COOH [ No CAS ]
CH₃C(O)-Aib-Pro-Aib-Ala-Aib-Ala-Gln(Trt)-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu(O-t-Bu)-Gln(Trt)-Phe-C(O)-(N²-biotinoylhydrazino-) [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2635 - 2639

9
[ 851138-53-9 ]
[ 66640-86-6 ]
[ 845869-41-2 ]

Yield	Reaction Conditions	Operation in experiment
		Terthiophenes 1 and 2 were prepared by the sequence shown in Figure 1. The 3'- (2-hydroxyethyl)-2, 2' : 5', 2"-terthiophene was prepared by a modified literature method (Scheib and BaeUERLE, 1999; Higgins et AL, 2001), and esterified with excess succinyl chloride to give 1 after workup. Terthiophene 1 was activated with 1,2, 2,2- tetrachloroethyl-N-succinimidyl carbonate (Jaouadi et AL, 1987), then reacted with commercially-available <strong>[66640-86-6]biotin hydrazide</strong> to give 2.

Reference： [1]Journal of Materials Chemistry,2005,vol. 15,p. 1186 - 1196
[2]Patent: WO2005/19210,2005,A1 .Location in patent: Page/Page column 9; Figure 1

10
fucan B, MW = 21.5 kDa [ No CAS ]
[ 66640-86-6 ]
biotinylated fucan B [ No CAS ]

Reference： [1]Planta Medica,2005,vol. 71,p. 628 - 633

11
5\-d(CTCCCAGGCXCA), X = 2\-O-(2-oxoethyl)arabinouridine [ No CAS ]
[ 66640-86-6 ]
5-d(CTCCCAGGCXCA), X = 2-O-(2-[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]hydrazono}ethyl)arabinouridine [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2005,vol. 54,p. 238 - 246

12
5\-d(CXCCCAGGCTCA), X = 2\-O-(2-oxoethyl)arabinouridine [ No CAS ]
[ 66640-86-6 ]
5-d(CXCCCAGGCTCA), X = 2-O-(2-[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]hydrazono}ethyl)arabinouridine [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2005,vol. 54,p. 238 - 246

13
5\-d(CXCCCAGGCXCA), X = 2\-O-(2-oxoethyl)arabinouridine [ No CAS ]
[ 66640-86-6 ]
5-d(CXCCCAGGCXCA), X = 2-O-(2-[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]hydrazono}ethyl)arabinouridine [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2005,vol. 54,p. 238 - 246

14
N-(2-oxo-ethyl)-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzamide [ No CAS ]
[ 66640-86-6 ]
N-(2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoyl]-hydrazono}-ethyl)-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzamide [ No CAS ]

Reference： [1]Heterocycles,2005,vol. 66,p. 531 - 534

15
[ 952210-10-5 ]
[ 66640-86-6 ]
C₈₈H₁₂₂N₄O₂₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In methanol; at 60℃; for 72h;	Aldehyde (16) (90 mg, 0.062 mmol) and (+) -<strong>[66640-86-6]biotin hydrazide</strong>(16.1 rag, 0.062 mmol) were combined in CH3OH (4 mL) and heated for 72 hr at 60 0C. After evaporation of the solvent, the crude material was purified by silica flash chromatography [CH2Cl2- CH3OH (10:1), R.f = 0.51]. The fractions containing product were collected and the solvent removed in vacuo to give the (19) (103 mg, 98 percent) ;HRMS-ES" (m/z) : [M] Na2+ calcd for [C88H122N4O26S]2+: 852.9034; found 853.9055.

Reference： [1]Patent: WO2007/113575,2007,A2 .Location in patent: Page/Page column 58; 60

16
CTCCCAGGC-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CA [ No CAS ]
[ 66640-86-6 ]
CTCCCAGGC-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH₂)arabinouridine]-CA [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7327 - 7330

17
C-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CCCAGGCTCA [ No CAS ]
[ 66640-86-6 ]
C-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH₂)arabinouridine]-CCCAGGCTCA [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7327 - 7330

18
C-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CCCAGGC-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-(2-oxoethyl)arabinouridine]-CA [ No CAS ]
[ 66640-86-6 ]
C-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH₂)arabinouridine]-CCCAGGC-[N³-(2,4-dinitrophenylsulfenyl)-2'-O-((+)-biotinylNHN=CHCH₂)arabinouridine]-CA [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7327 - 7330

19
C₂₇H₃₇NO₆S [ No CAS ]
[ 66640-86-6 ]
C₃₇H₅₃N₅O₇S₂ [ No CAS ]

Reference： [1]Journal of Pharmacology and Experimental Therapeutics,2007,vol. 321,p. 1023 - 1031

20
[ 66640-86-6 ]
schizophyllan [ No CAS ]
schizophyllan-biotin [ No CAS ]

Reference： [1]Biological and Pharmaceutical Bulletin,2007,vol. 30,p. 1384 - 1389

21
[ 1000783-83-4 ]
[ 66640-86-6 ]
C₁₆₄H₂₈₂N₁₂O₄₄S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 8801 - 8810

22
C₁₅₂H₂₆₃N₁₁O₄₁ [ No CAS ]
[ 66640-86-6 ]
C₁₆₂H₂₇₉N₁₅O₄₂S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 8801 - 8810

23
[ 1012043-27-4 ]
[ 66640-86-6 ]
[ 1012043-29-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 650 - 652

24
[ 1070418-04-0 ]
[ 66640-86-6 ]
C₅₉H₈₃N₁₆O₂₀PS [ No CAS ]

Reference： [1]Organic Letters,2008,vol. 10,p. 4605 - 4608

25
C₂₉H₃₅F₃N₄O₁₂S [ No CAS ]
[ 66640-86-6 ]
C₃₉H₅₁F₃N₈O₁₃S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%		EXAMPLE 23Manufacture of the Compound (28) from the Compounds (26) and (27)The compound (26) (72 mg, 0.1 mmol) was dissolved in 1 ml of dichloromethane, then N-hydroxysuccinimide (13 mg, 0.11 mmol) and DCC (23 mg, 0.11 mmol) were added thereto and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated therefrom under reduced pressure, the residue was dissolved in DMSO (1 ml), <strong>[66640-86-6]biotin hydrazide</strong> (compound (27)) (26 mg, 0.1 mmol) was added thereto and the mixture was stirred overnight at room temperature. The reaction solution was directly purified by a silica gel column chromatography (eluting with chloroform:methanol=5:1) to give the compound (28) (10 mg, 10percent) as a pale yellow solid. Positive ion FABMS (3-nitrobenzylalcohol) m/z: 961 (M+H)+.

Reference： [1]Patent: US6903223,2005,B1 .Location in patent: Page/Page column 20

26
[ 1002342-83-7 ]
[ 66640-86-6 ]
[ 1207091-93-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; dichloromethane; water; at 20℃; for 16h;	Preparation of iV-(2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy) acetaldehyde Biotinyl- hydrazone (1). To an anhydrous CH2Cl2 solution (2 mL) of oxalyl chloride (0.10 mL, 1.10 mmol) maintained at -78 °C under Ar was slowly added freshly distilled DMSO (0.19 mL, 3.29 mmol). The mixture was stirred (30 min), and then dry 4 (0.20 g, 0.91 mmol) was added via syringe. The mixture was stirred for an additional 30 min at -78 °C, and then Et3N (0.78 mL, 6.57 mmol) was added (10 min) and the mixture was stirred (15 min) at this temperature and warmed to ambient temperature. The reaction solution was diluted with CH2Cl2 (10 mL) and washed with H2O (2 x 10 mL). The organic layer was dried (Na2SO4), concentrated, and the crude aldehyde 5 (0.19 g, 0.88 mmol) was dissolved in CH2Cl2 (1 mL) and added to a solution of 6 (0.15 g, 0.58 mmol) in THFVH2O (1 : 1, 5 mL). The reaction mixture was allowed to stir at room temperature (16 h), the solvent was evaporated in vacuo, and then the crude product purified by column chromatography (SiO2; 1/9 MeOH/CHCl3) to yield 0.20 g (74percent) of 1 as a white solid: mp 134-135 0C; R1= 0.35 (1/9 MeOH/CHCl3); IR (nujol) 2924, 2101, 1667, 1557, 1459 cm"1; 1H NMR (CD3OD) (minor conformer in parenthesis (a mixture of conformers similar to other hydrazones (Syakaev et al. 2006))) delta 1.45-1.52 (m, C(6)H2), 1.58-1.79 (m, C(7)H2, C(8)H2), 2.27 (t, J = 7.4 Hz, C(9)H2 (2.65 (t, J = 7.5 Hz, C(9)H2))), 2.71 (d, J- 12.6 Hz, C(5)HH'), 2.93 (dd, J= 4.7, 12.6 Hz, C(5)HH'), 3.18-3.25 (m, C(2)H), 3.37 (t, J = 4.8 Hz, N3CH2), 3.65-3.69 (m, 2 OCH2CH2O, N3CH2CH2), 4.18 (d, J = 5.3 Hz, OCH2CHN (4.15 (d, J= 5.3 Hz, OCH2CHN))), 4.31 (dd, J- 4.2, 7.6 Hz, C(3)H), 4.49 (dd, J = 4.7, 7.6 Hz, C(4)H), 7.49 (t, J= 5.3 Hz, OCH2CHN (7.33 (t, J= 5.3 Hz, OCH2CHN))); 13C NMR (CD3OD) (minor conformer in parenthesis) delta 26.0 (26.6) (C(6)), 29.6 (C(7)), 29.9 (30.0) (C(8)), 33.2 (35.2) (C(9)), 41.2 (C(5)), 51.9 (N3CH2), 57.1 (57.2) (C(2)), 61.8 (C(3)), 63.5 (C(4)), 71.2, 71.3, 71.4, 71.5, 71.7, 71.8 (3 CH2OCH2), 145.6 (149.3) (OCH2CHN), 166.3 (C(2')), 172.7 (177.9) (C(IO)); HRMS (ESI) 458.2182 [M + H+] (calcd. for Ci8H32N7O5S 458.2186); Anal. (C18H3iN7O5S, 0.25 H2O) Calcd.: C, 46.79percent; H, 6.87percent; N, 21.22percent; S, 6.94percent. Found: C, 46.67percent; H, 6.82percent; N, 20.88percent; S, 6.88percent.

Reference： [1]Patent: WO2010/14236,2010,A2 .Location in patent: Page/Page column 23-24

27
C₈₅H₉₀N₂O₂₆S₂ [ No CAS ]
[ 66640-86-6 ]
[ 1227413-17-3 ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 979 - 987

28
C₂₅H₂₁NO₈S₂ [ No CAS ]
[ 66640-86-6 ]
C₃₁H₃₄N₄O₇S₃ [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 979 - 987

29
[ 1227413-32-2 ]
[ 66640-86-6 ]
[ 1227413-14-0 ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 979 - 987

30
[ 3326-32-7 ]
[ 66640-86-6 ]
C₃₁H₂₉N₅O₇S₂ [ No CAS ]

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 979 - 987

31
[ 91853-90-6 ]
[ 66640-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate;Heating;	To a suspension of homobiotin 14b (150 mg, 0.58 mmol) in dry methanol (1.5 ml) was added drop-wise thionyl chloride (276 mg, 169 muL, 2.32 mmol) and stirred under a nitrogen atmosphere for 2 h. The mixture was concentrated in vacuo, suspended in methanol (2 ml) and was added hydrazine hydrate (0.5 ml) and stirred for 16 h. The reaction mixture was concentrated in vacuo, dissolved in water (5 ml) and washed with chloroform (2 x 5 ml). The aqueous layer was concentrated in vacuo to give a white powder (121 mg, 77percent).

Reference： [1]Bioconjugate Chemistry,2010,vol. 21,p. 979 - 987
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4689 - 4693

32
[ 1395347-05-3 ]
[ 66640-86-6 ]
C₂₂H₃₀N₄O₂S₄ [ No CAS ]

Reference： [1]Macromolecules,2012,vol. 45,p. 6766 - 6773,8

33
[ 1226145-00-1 ]
[ 66640-86-6 ]
C₂₀H₂₂Cl₂N₄O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethylsulfoxide-d6; at 20℃; for 96h;	General procedure: To a solution of beta-keto ester 4 (100 mg, 0.38 mmol) in EtOH (10 mL) was added the substituted hydrazine (2 equiv. 0.76 mmol) and the solution stirred at room temperature over night. The solvent was removed in vacuo and the residue purified by column chromatography (20:1 DCM:MeOH) to provide the title compound. NMR data is reported for the major tautomer observed.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6647 - 6650

34
[ 66640-86-6 ]
chondroitin disaccharide 0-S [ No CAS ]
[ 1419703-15-3 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 11800 - 11804
Angew. Chem.,2012,vol. 124,p. 11970 - 11974,5

35
(-)-brevenal [ No CAS ]
[ 66640-86-6 ]
C₄₉H₇₆N₄O₉S [ No CAS ]

Reference： [1]Journal of Natural Products,2014,vol. 77,p. 2014 - 2020

36
[ 1428361-03-8 ]
[ 66640-86-6 ]
[ 1428360-83-1 ]
3-[4-[5-[4-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]butyl]-1H-1,2,4-triazol-3-yl]butyl]-5-methyl-1,3-benzoxazol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; toluene; at 150℃; for 2h;Microwave irradiation;	To a suspension of <strong>[66640-86-6]biotin hydrazide</strong> 15a2 (28 mg, 0.108 mmol) in anhydrous DMF (0.5 ml) were added imidic ester 19 (32 mg, 0.102 mmol), DIPEA (52 mg, 0.410 mmol) and anhydrous toluene (0.5 ml). The mixture was stirred and microwaved at 150 oC for 2 h (with variable pressure and power), concentrated in vacuo and purified by silica gel chromatography eluting with 5percent methanol in dichloromethane to give 1,2,4-oxadiazole 5 (16 mg, 33percent) and eluting at 12percent methanol in dichloromethane to give 1,2,4-triazole 3 (7 mg, 15percent)

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4689 - 4693

37
[ 58-85-5 ]
[ 66640-86-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4689 - 4693
[2]Journal of the American Chemical Society,2014,vol. 136,p. 18140 - 18148
[3]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 707 - 712

38
C₁₅₃H₂₂₅N₄₃O₄₈S [ No CAS ]
[ 66640-86-6 ]
HSQGTFTSDYSKY-((2S)-N-[(1S,3E)-3-({5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}imino)-1-carbamoylpropyl]-2-amino-4-methylpentanamide)-SRRAQDFVQWLMNT [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 18140 - 18148

39
[ 1613697-49-6 ]
[ 66640-86-6 ]
C₆₈H₈₉N₅O₁₉S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With pyridine; In dimethyl sulfoxide; at 0 - 20℃; for 96h;	A solution of SB-T-1214-(SS-linker OSu (0.069 g, 0.269 mmol) and <strong>[66640-86-6]biotinylhydrazine</strong> (0.336 g, 0.269 mmol) in a 3:1 mixture of DMSO-pyridine (2.7 mL) was cooled to 0 °C, and the mixture was reacted for 4 d at room temperature. Purification of the crude product by column chromatography on silica gel with 7percent CH3OH in CH2C12 as eluent gave 15 (0.175 g, 47percent) as a white solid: 1H NMR (400 MHz, CD3OD) delta 1.02 (m, 2H), 1.10 (m, 2H), 1.20 (s, 6H), 1.30 (d, J = 6.8 Hz, 3H), 1.44 (s, 9H), 1.49 (m, 2H), 1.63 (m, 4H), 1.68 (s, 3H), 1.76 (s, 3H), 1.78 (s, 3H), 1.81 (m, 3H), 1.94 (s, 3H), 1.99 (m, 2H), 2.28 (t, J = 7.6 Hz, 2H), 2.35 (m, 2H), 2.41 (s, 3H), 2.48 (m, 2H), 2.71 (d, J= 12 Hz, 1H), 2.93 (dd, J= 5.0, 12.7 Hz, 1H), 2.98 (m, 1H), 3.22 (m, 1H), 3.87 (d, J= 7.2 Hz, 1H), 4.03 (d, J= 2.4, 16.7, 1H), 4.13 (d, J= 1.8, 16.7 Hz, 1H), 4.20 (d, J = 8.4 Hz, 1H), 4.24 (d, J= 8.4 Hz, 1H), 4.32 (m, 2H), 4.50 (dd, J= 4.4, 8.0 Hz, 1H), 4.59 (s, 2H), 4.94 (d, J= 2.4 Hz, 2H), 5.03 (d, J= 7.6 Hz, 1H), 5.28 (bs, 1H), 5.69 (d, J= 7.2 Hz, 1H), 6.16 (bt, J= 9.0 Hz, 1H), 6.48 (s, 1H), 7.33 (m, 3H), 7.53 (t, J= 8.0 Hz, 2 Hz), 7.66 (t, J= 7.4 Hz, 1H), 7.83 (d, J= 7.8 Hz, 1H), 8.15 (d, J = 7.2 Hz, 2H); 13C NMR (125 MHz, CD3OD) delta 7.81, 7.84, 9.06, 12.41, 13.64, 17.27, 19.46, 19.57, 20.99, 21.89, 24.73, 24.98, 25.59, 27.41, 27.96, 28.14, 30.61, 30.90, 32.98, 35.35, 36.14, 38.13, 39.03, 39.67, 43.20, 45.78, 45.90, 46.68, 49.32, 55.54, 57.88, 60.25, 61.85, 70.92, 71.58, 74.92, 75.18, 75.34, 76.06, 77.70, 79.11, 80.93, 84.49, 119.83, 127.51, 128.06, 128.30, 129.75, 130.01, 130.09, 130.12, 131.01, 133.19, 133.37, 133.53, 137.28, 137.40, 137.54, 141.24, 156.09, 164.75, 166.20, 168.91, 170.08, 170.10, 170.89, 172.67, 173.47, 173.72, 203.76; HRMS (TOF) for C68H9oN5019S3+ calcd: 1376.5387. Found: 1376.5397 (Delta = 0.7 ppm). HPLC (A): RT = 12.1 min, purity > 99percent.

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2406 - 2416
[2]Patent: WO2015/143092,2015,A1 .Location in patent: Paragraph 0103

40
C₆₂H₇₄F₂N₂O₂₀S₂ [ No CAS ]
[ 66640-86-6 ]
C₆₈H₈₇F₂N₅O₁₉S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With pyridine; In dimethyl sulfoxide; at 0 - 20℃; for 72h;	To a solution of 15 (87 mg, 0.069 mmol) and 16 (28 mg, 0.11 mmol) in DMSO (0.5 mL) at 0 °C was added pyridine (0.15 mL), and the mixture was allowed to warm from 0 °C to room temperature and react for 72 h with stirring. The reaction mixture was directly concentrated in vacuo to afford a yellow-green oil. Purification of the crude product by column chromatography on silica gel with 6percent CH3OH in CH2Cl2 as eluent gave BLT-F2 (1) as a white solid (62 mg, 77percent): mp 129-131 °C; 1H NMR (500 MHz, CD3OD): delta 1.03-1.24 (m, 4H), 1.23 (s, 3H), 1.24-1.32 (m, 5H), 1.38-1.70 (m, 4H), 1.33 (s, 3H), 1.42 (s, 9H), 1.60-1.72 (m, 1H), 1.74 (s, 3H), 1.81 (m, 1H), 1.83 (s, 3H), 1.84 (s, 3H), 1.92 (m, 1H), 1.97 (s, 3H), 2.11 (m, 3H), 2.24-2.52 (m, 4H), 2.42 (s, 3H), 2.54-2.72 (m, 2H), 2.83 (br s, 4H), 2.87 (m, 2H), 3.22 (m, 1H), 3.88 (d, J = 7.2 Hz, 1H), 3.93 (s, 2H), 4.21 (d, J = 8.4 Hz, 1H), 4.27 (d, J = 8.4 Hz, 1H), 4.48 (dd, J = 6.6, 10.5 Hz, 1H), 4.74-4.32 (m, 1H), 4.49 (m, 1H), 4.88 (m, 2H), 5.05 (d, J = 8.1 Hz, 1H), 5.39 (d, J = 6.0 Hz, 1H), 5.70 (d, J = 7.2 Hz, 1H), 6.23 (t, J = 9.0 Hz, 1H), 6.37 (s, 1H), 6.94 -7.02 (m, 2H), 7.381 (t, J = 8.4 Hz, 1H), 7.53 (m, 1H), 7.75 (dd, J = 6.0, 8.4 Hz, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.97 (d, J = 7.8 Hz, 1H); 13C NMR (125 MHz, CD3OD): delta 7.78, 8.99, 12.38, 13.59, 17.22, 19.41, 19.49, 20.93, 24.96, 25.55, 27.36, 27.94, 29.35, 30.53, 30.90, 32.96, 35.35, 36.11, 38.15, 39.03, 39.64, 43.16, 45.72, 46.67, 49.30, 55.51, 57. 86, 60.26, 61.84, 70.15, 70.91, 71.59, 75.32, 75.44, 75.94, 77.69, 79.11 80.96, 84.45, 114.87, 115.09, 116.11, 116.34, 117.68, 117.91, 119.78, 119.93, 120.15, 125.68, 130.29, 130.37, 132.32, 132.39, 132.97, 133.36, 133.45, 136.67, 137.30, 141.25, 156.09, 161.16, 161.37, 163.60, 163.81, 164.74, 164.88, 168.82, 169.98; 19F NMR (376 MHz, CD3OD): delta -112.95 (s, 1F), -111.88 (s, 1F). HRMS (TOF): Calcd. for C68H88F2N5O19S3+: 1412.5204: Found: 1412.5159 (Delta = -3.2 ppm).

Reference： [1]Journal of Fluorine Chemistry,2015,vol. 171,p. 148 - 161

41
[ 66640-86-6 ]
C₂₉H₃₈N₄O₁₂Rh₂S [ No CAS ]
C₂₉H₃₈N₄O₁₂Rh₂S [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2033 - 2038

42
[ 66640-86-6 ]
[ 619-05-6 ]
C₁₇H₂₄N₆O₃S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 9270 - 9272

43
[ 1571-30-8 ]
[ 66640-86-6 ]
C₂₀H₂₃N₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		To a suspension of 8-hydroxyquinoline-2-carboxylic acid (51mg, 0.27mmol) in dry DMF (7mL) were added 1-hydroxybenzotriazole monohydrate (37mg, 0.27mmol) and DCC (56mg, 0.27mmol). After 1h, <strong>[66640-86-6]biotin hydrazide</strong> (70mg, 0.27mmol) was added. The reaction mixture was stirred for 48h at room temperature, filtered off and then evaporated to dryness. The crude product was purified by precipitation in water and then silica flash chromatography (dichlromethane/methanol 98:2). (0045) Yield: 64mg (55percent); Positive ion ESI-MS: m/z=430.0 [P+H]+, 452.1 [P+Na]+, 468.1 [P+K]+, 880.9 [2P+Na]+, 896.9 [2P+K]+; 1H NMR (500MHz, (CD3)2SO) delta (ppm): 11.20 (s, 1H, NH), 10.18 (s, 1H, OH), 10.04 (s, 1H, NH), 8.53 (d, 1H, J4,3=8.6Hz, H-4 of HQ), 8.12 (d, 1H, J4,3=8.6Hz, H-3 of HQ), 7.59 (t, 1H, J=7.9Hz, H-6 of HQ), 7.50 (dd, 1H, J5,6=8.2Hz, J5,7=1.2Hz, H-5 of HQ), 7.18 (dd, 1H, J7,6=7.6Hz, J7,5=1.2Hz, H-7), 6.45 (s, 1H, NH of biotin), 6.38 (s, 1H, NH of biotin), 4.32 (m, 1H, H-9 of biotin), 4.16 (m, 1H, H-10 of biotin), 3.14 (m, 1H, H-6 of biotin), 2.84 (dd, 1H, J8,8?=12.5 and J8,9=5.1Hz, H-8 of biotin), 2.59 (d, 1H, J8?,8=12.5Hz, H-8? of biotin), 2.25 (m, 2H, Hs-2 of biotin), 1.61 (m, 3H, H-5 and Hs-3 of biotin), 1.45 (m, 3H, Hs-4 and H-5? of biotin); 13C NMR (125MHz, (CD3)2SO) delta (ppm): 171.9 (C=O groups), 162.9 (C-12 of biotin), 153.9 (C-8 of HQ), 146.7 (C-2 of HQ), 138.3 (C-4 of HQ), 136.6 (C-9 of HQ), 130.0 (C-10 and C-6 of HQ), 119.3 (C-3 of HQ), 118.0 (C-5 of HQ), 112.2 (C-7 of HQ), 61.6 (C-10 of biotin), 59.6 (C-9 of biotin), 55.9 (C-6 of biotin), 40.4 (C-8 of biotin), 33.5 (C-2 of biotin), 28.4 (C-4 and C-5 of biotin), 25.6 (C-3 of biotin).

Reference： [1]Polyhedron,2016,vol. 110,p. 254 - 260

44
[ 14510-06-6 ]
[ 66640-86-6 ]
8-hydroxyquinolylbiotin hydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	In ethanol; for 24h;Reflux;	8-Hydroxy-2-quinolinecarboxaldehyde (47mg, 0.27mmol) was added to <strong>[66640-86-6]biotin hydrazide</strong> (70mg, 0.27mmol) in absolute ethanol (25mL). The reaction was refluxed under stirring for 24h. After cooling, the product precipitated and then was collected by filtration and recrystallized from ethanol. (0047) Yield: 88mg (79percent); Positive ion ESI-MS: m/z=414.1 [P+H]+, 436.1 [P+Na]+, 826.8 [2P+H]+, 848.8 [2P+Na]+; 1H NMR (500MHz, (CD3)2SO) delta (ppm): 11.70 (s, NH, isomer B), 11.64 (s, NH, isomer A), 9.79 (s, OH), 8.36 (s, CH=N, isomer B), 8.31 (d, J4,3=8.7Hz, H-4 of HQ), 8.21 (s, CH=N, isomer A), 8.02 (m, H-3 of HQ), 7.49?7.34 (m, H-5 and H-6 of HQ), 7.11 (t, J=7.0Hz, H-7), 6.42 (s, H-11 of biotin), 6.34 (s, H-13 of biotin), 4.31 (m, H-9 of biotin), 4.15 (m, H-10 of biotin), 3.14 (m, H-6 of biotin), 2.82 (m, H-8 of biotin), 2.72 (t, J=7.4Hz, Hs-2 of biotin, isomer A), 2.58 (m, H-8? of biotin), 2.28 (m, H-2 of biotin, isomer B), 1.67 (m, H-5 and Hs-3 of biotin), 1.59?1.35 (m, Hs-4 and H-5? of biotin). 13C NMR (125MHz, (CD3)2SO) delta (ppm): 175.2 (C=O, isomer A), 169.13 (C=O, isomer B), 163.2 (C-12 of biotin), 154.1 (C-8 of HQ), 152.1 (C-2 of HQ), 146.6 (CH=N, isomer B), 143.2 (CH=N, isomer A), 138.6 (C-9 of HQ), 136.9 (C-4 of HQ), 135.0 (C-10 of HQ), 128.5 (C-6 of HQ), 118.0 (C-3 and C-5 of HQ), 112.5 (C-7 of HQ), 61.4 (C-10 of biotin), 59.6 (C-9 of biotin), 55.8 (C-6 of biotin), 40.2 (C-8 of biotin), 34.4 (C-2 of biotin, isomer B), 32.1 (C-2 of biotin, isomer A), 28.6 (C-4 and C-5 of biotin), 24.9 (C-3 of biotin).

Reference： [1]Polyhedron,2016,vol. 110,p. 254 - 260

45
[ 1610596-19-4 ]
[ 66640-86-6 ]
(9H-fluoren-9-yl)methyl 1,2-dimethyl-2-((1-(3-oxo-3-(2-(5-((3aS,4R,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)hydrazinyl)propyl)-1H-indol-2-yl)methyl)hydrazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.18 g	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 19h;	j00086j A solution of 5-((3 aS,4S,6aR)-2-oxohexahydro- 1 H-thieno [3 ,4-d]imidazol- 4-yl)pentanehydrazide (0.10 g, 0.39 mmol ), (9H-fluoren-9-yl)methyl 1,2-dimethyl-2- ((1 -(3 -oxo-3 -(perfluorophenoxy)propyl)- 1 H-indol-2-yl)methyl)hydrazine- 1- carboxylate (0.28 g, 0.43 mmol) and DIPEA (0.14 g, 1.04 mmol) in DMF (1.94 mE) was stirred in room temperature for 19 h. The mixture was concentrated under reduced pressure, and then was purified by Cl 8 silica gel chromatography (0- 10 percent MeOH in dichloromethane) to give(9H-fluoren-9-yl)methyl 1 ,2-dimethyl-2-(( 1-(3 -oxo-3 -(2-(5-((3 aS,4R,6aR)-2-oxohexahydro- 1 H-thieno [3 ,4-d] imidazol-4-yl)pentanoyl)hydrazinyl)propyl)- 1 H-indol-2-yl)methyl)hydrazine- 1 -carboxylate (2a) (0.18 g). ESI-MS: mlz 724 (M + H)+.

Reference： [1]Patent: WO2016/109802,2016,A1 .Location in patent: Paragraph 00084; 00085; 00086

46
[ 41991-02-0 ]
[ 66640-86-6 ]
C₁₅H₂₀N₄O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		To a solution of 202 mg (1 mmol, 1 eq) of 2,5-dimethoxy-2,5-dihydron acetate in furolide was added 4 mL0.1 M aqueous HCI was stirred at room temperature for 3 h. The reaction system was neutralized to neutral with sodium bicarbonate solids and 0.4 mL of 500 mM was addedHEPES buffer (50 mM, pH 7.5) to adjust the pH to 7.5. To the resulting mixture was added 129 mg (0.5 mmol, 0.5 eq)A solution of <strong>[66640-86-6]biotin hydrazide</strong> in DMSO (3 mL) was reacted at room temperature for 1 h. Part of the solvent was removed by steaming and the remaining solution was filtered with reverse phase HPLCTo give 71 mg (0.21 mmol, yield 42percent) of brown solid.

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 6146 - 6151
[2]Patent: CN106748955,2017,A .Location in patent: Paragraph 0085; 0086; 0087; 0088; 0089; 0090; 0091

47
[ 57683-72-4 ]
[ 66640-86-6 ]
C₂₀H₂₉N₅O₁₁S₂ [ No CAS ]

Reference： [1]ChemBioChem,2017,vol. 18,p. 1688 - 1691

48
[ 66640-86-6 ]
C₁₉H₂₂O₁₁Rh₂ [ No CAS ]
C₂₉H₃₈N₄O₁₂Rh₂S [ No CAS ]

Reference： [1]Catalysis science and technology,2018,vol. 8,p. 2294 - 2298

49
[ 66640-86-6 ]
C₁₉H₂₂O₁₁Rh₂ [ No CAS ]
C₂₉H₃₈N₄O₁₂Rh₂S [ No CAS ]

Reference： [1]Catalysis science and technology,2018,vol. 8,p. 2294 - 2298

50
[ 66640-86-6 ]
C₃₀H₄₈N₉O₉Pol [ No CAS ]
C₄₀H₆₄N₁₃O₁₀PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	General procedure: Fully-protected thymopentin attached to a resin was synthesizedby standard SPPS. Fmoc-protected amino acid (0.2 mmol)was anchored to Wang resin (0.05 mmol) by using EDC/HOBt(0.2 mmol) in DMF (4 mL), and the Fmoc group was removed bytreatment with 20 vol percent piperidine in DMF (5 mL). To removethe OAll group, the resin was treated with Pd(PPh3)4 (0.2 mmol)and PhSiH3 (0.5 mmol) in CH2Cl2 (4 mL). The mixture wasshaken at r.t. for 12 h. The solvent was then removed by filtration,and the resin was washed with CH2Cl2 (3 × 5 mL) and DMF (3 × 5 mL). Side-chain modifications were performed by usingvarious modifiers under the appropriate conditions (Scheme 1).For TA1, MPEG6-OH (0.2 mmol), HOBt (0.2 mmol), DIC (0.2mmol), DMAP (0.1 mmol) were dissolved in DMF (4 mL). ForTA2?TA6: R?H (0.2 mmol), HOBt (0.2 mmol), HBTU (0.2 mmol),and DIPEA (0.2 mmol) were dissolved in DMF (4 mL) [R?H = e.g.,MPEG6-NH2, glucosamine·HCl, 2-(biotinamido)ethylamine,<strong>[66640-86-6]biotin hydrazide</strong>, or dansylhydrazine]. For all reactions, thereaction mixture was shaken at r.t. for 24 h. The solvent wasremoved by filtration and the resin was washed with CH2Cl2(3 × 5 mL) and DMF (3 × 5 mL). The resin was then suspended in20percent piperidine/DMF for 30 min to remove the Fmoc group. Thepeptide was cleaved from the resin with 50 vol percent TFA in CH2Cl2(5 mL) for 2 h. The residue was dissolved in H2O then freezedriedto give the solid. The crude product was finally purified bypreparative RP-HPLC.

Reference： [1]Synlett,2018,vol. 29,p. 2588 - 2594

51
[ 66640-86-6 ]
[ 148-53-8 ]
C₁₈H₂₄N₄O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; for 5h;Reflux;	Weigh 2.58 g of <strong>[66640-86-6]biotin hydrazide</strong> and 1.52 g of o-vanillin in a container.Add 150 mL of ethanol and reflux for 5 h to obtain a yellow solid product.The yield was 78percent.

Reference： [1]Patent: CN108558914,2018,A .Location in patent: Paragraph 0032; 0033; 0034

52
[ 23605-05-2 ]
[ 66640-86-6 ]
C₃₉H₅₈N₄O₁₂S [ No CAS ]
C₃₉H₅₈N₄O₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In methanol; at 60℃; for 10h;	General procedure: Biotinylatedcardiac glycoside chemical probes were synthesize following the nucleophilicaddition reaction, and subsequent dehydration under the catalysis of 1percent AcOH. To asolution of cardiac glycoside (beta-Antiarin or alpha-Antiarin, 1 eq.) and Biotin-linkerproduct (Biotinylhydrazine, Biotin-AAn-CONHNH2 and Biotin-PEG(n+1)-CONHN2,about 7 eq.) in MeOH was added 1percent AcOH. The reaction mixture was stirred andrefluxed for 10h at 60°. The crude product was obtained by concentrated underreduced pressure. The residue was purified by semipreparative RP-HPLC (17percentACN-H2O or 35percent MeOH-H2O) to obtain Biotinylated cardiac glycoside chemicalprobes (P1a-P8a and P1b-P8b).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 707 - 712

53
[ 639-13-4 ]
[ 66640-86-6 ]
C₃₉H₅₈N₄O₁₂S [ No CAS ]
C₃₉H₅₈N₄O₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In methanol; at 60℃; for 10h;	General procedure: Biotinylatedcardiac glycoside chemical probes were synthesize following the nucleophilicaddition reaction, and subsequent dehydration under the catalysis of 1percent AcOH. To asolution of cardiac glycoside (beta-Antiarin or alpha-Antiarin, 1 eq.) and Biotin-linkerproduct (Biotinylhydrazine, Biotin-AAn-CONHNH2 and Biotin-PEG(n+1)-CONHN2,about 7 eq.) in MeOH was added 1percent AcOH. The reaction mixture was stirred andrefluxed for 10h at 60°. The crude product was obtained by concentrated underreduced pressure. The residue was purified by semipreparative RP-HPLC (17percentACN-H2O or 35percent MeOH-H2O) to obtain Biotinylated cardiac glycoside chemicalprobes (P1a-P8a and P1b-P8b).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 707 - 712

54
[ 66640-86-6 ]
C₃₉H₁₉N₉OSZn [ No CAS ]
C₄₉H₃₇N₁₃O₃S₂Zn [ No CAS ]

Reference： [1]Journal of Porphyrins and Phthalocyanines,2019,vol. 23,p. 125 - 135

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 66640-86-6 ] {[proInfo.proName]}

Quality Control of [ 66640-86-6 ]

Related Doc. of [ 66640-86-6 ]

Product Details of [ 66640-86-6 ]

Calculated chemistry of [ 66640-86-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 66640-86-6 ]

Application In Synthesis of [ 66640-86-6 ]

[ 66640-86-6 ] Synthesis Path-Upstream 1~3

[ 66640-86-6 ] Synthesis Path-Downstream 1~54

Related Functional Groups of [ 66640-86-6 ]

Amides

Amines

Related Parent Nucleus of [ 66640-86-6 ]

Aliphatic Heterocycles

Other Aliphatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 66640-86-6 ]

Related Parent Nucleus of
[ 66640-86-6 ]