[ CAS No. 363191-25-7 ] {[proInfo.proName]}

Name: 363191-25-7|H-D-Dap(Boc)-OMe|97%
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Quality Control of [ 363191-25-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 363191-25-7 ]

CAS No. :	363191-25-7	MDL No. :	MFCD11100944
Formula :	C₉H₁₈N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AXLHVTKGDPVANO-ZCFIWIBFSA-N
M.W :	218.25	Pubchem ID :	7018226
Synonyms :

Calculated chemistry of [ 363191-25-7 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	53.88
TPSA :	90.65 Å²

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) :	-7.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	-0.06
Log Po/w (WLOGP) :	0.01
Log Po/w (MLOGP) :	0.01
Log Po/w (SILICOS-IT) :	-0.38
Consensus Log Po/w :	0.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.69
Solubility :	44.2 mg/ml ; 0.203 mol/l
Class :	Very soluble
Log S (Ali) :	-1.39
Solubility :	8.84 mg/ml ; 0.0405 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.01
Solubility :	21.3 mg/ml ; 0.0977 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.77

Safety of [ 363191-25-7 ]

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

Application In Synthesis of [ 363191-25-7 ]

* 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 [ 363191-25-7 ]
Downstream synthetic route of [ 363191-25-7 ]

[ 363191-25-7 ] Synthesis Path-Upstream 1~2

1
[ 96136-12-8 ]
[ 363191-25-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2409 - 2421
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5455 - 5461

2
[ 24424-99-5 ]
[ 363191-25-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2409 - 2421

[ 363191-25-7 ] Synthesis Path-Downstream 1~30

1
[ 80466-79-1 ]
[ 363191-25-7 ]
methyl N²-(3,5-dimethylisoxazol-4-ylsulfonyl)-N³-Boc-(R)-2,3-diaminopropionate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1178 - 1192

2
[ 96136-12-8 ]
[ 363191-25-7 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5455 - 5461

3
[ 16133-25-8 ]
[ 363191-25-7 ]
3-<i>tert</i>-butoxycarbonylamino-2-(pyridine-3-sulfonylamino)-propionic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

4
[ 24424-99-5 ]
[ 363191-25-7 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2409 - 2421

5
[ 15764-16-6 ]
[ 363191-25-7 ]
C₁₈H₂₈N₂O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5455 - 5461

6
[ 1436426-21-9 ]
[ 363191-25-7 ]
[ 477199-77-2 ]
C₃₀H₃₈ClF₄N₅O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 4-(bromomethyl)-2-fluorobenzoic acid (0.76 g, 3.25 mmol) in CH2C12 (5 mL), was added oxalyl chloride (1.422 mL, 16.25 mmol) followed by a few drops of DMF at room temperature. The reaction was stirred for 1 h at room temperature. The reaction was concentrated under reduced pressure and the resulting residue was dissolved in CH2C12 (5 mL), and then 4-chloro-2-(4-(3,3,3-trifluoropropyl)piperazin-1-yl)aniline (1.0 g, 3.25 mmol) and DIEA (0.420 g, 3.25 mmol) were added. The reaction was stirred for 30 min at room temperature. The reaction was washed with water and dried over MgS04. The organic layer was concentrated under reduced pressure and the residue was crystallized in methanol. The precipitate was filtered and dried under reduced pressure to give the title compound (1.45 g, 85%) as a mixture of bromo- and chloro- intermediates. LC/MS (peak 1) m/z = 478.0 [M+H]+, (peak 2) m/z = 523.2 [M+H]+. Intermediate 2 (10 mg, 0.019 mmol), (R)-methyl 2-amino-3-(teri- butoxycarbonylamino)propanoate (4.17 mg, 0.019 mmol), and DIEA (3.34 mu?, 0.019 mmol) were added to a vial with DMF (0.4 mL). The reaction was heated to 80 C and stirred at this temperature for 1 h. After this time, the reaction was complete. The N-Boc protected intermediate was purified by preparative LC/MS (5-70% ACN/H20, 25 min). After lyophilization, the solid was re-dissolved in MeOH (0.4 mL) and TFA (0.1 mL) (to cleave the N-Boc group). The reaction was allowed to stir at room temperature over night. Then, the solvent was removed, the oil was re-dissolved in ACN (0.4 mL) and H20 (0.8 mL), frozen, and lyophilized to give the title compound. LC/MS m/z = 560.4 [M+H]+; lU NMR (400 MHz,DMSO-i ) delta ppm 1.21-1.31 (m, 1H), 2.75-2.91 (m, 3H), 3.05-3.20 (m, 2H), 3.33-3.81 (m, 17H), 7.29 (dd, = 8.84, 2.27 Hz, 1H), 7.36-7.43 (m, 2H), 7.47 (d, = 13.14 Hz, 1H), 7.89 (t, = 8.02 Hz, 1H), 8.30 (d, = 8.08 Hz, 1H), 9.65 (d, = 8.97 Hz, 1H).

Reference： [1]Patent: WO2013/70657,2013,A1 .Location in patent: Page/Page column 131;

7
[ 131543-46-9 ]
[ 76438-34-1 ]
[ 363191-25-7 ]
methyl (2R)-3-[(tert-butoxycarbonyl)amino]-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		To a solution of (2S)-2-tetrahydropyran-2-yloxypropanal (7.5 g) in MeOH (80 mL) were added glyoxal (4.2 mL) and methyl (2R)-2-amino-3-hydroxy-propanoate (8.0 g) in MeOH (40 mL) at room temperature. After stirring for 10 minutes, ammonium acetate (2.8 g) was added into the reaction mixture, which was stirred for additional 3 days and concentrated in vacuo. The residue was purified with OH-type silica gel column chromatography (10-100% EtOAc in n-hexane) to give the title compound (4.4 g, 30 % yield) as yellow amorphous. MS (ESI) m/z 398 [M+lh] RT = 0.559 min. LCMS condition : B.

Reference： [1]Patent: WO2018/216822,2018,A1 .Location in patent: Page/Page column 175

8
[ 363191-25-7 ]
tert-butyl [(2R,3E)-3-(hydroxyimino)-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)propyl]carbamate [ No CAS ]

Reference： [1]Patent: WO2018/216822,2018,A1

9
[ 363191-25-7 ]
tert-butyl [(2R)-2-(5-iodo-1,2-oxazol-3-yl)-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)ethyl]carbamate [ No CAS ]

Reference： [1]Patent: WO2018/216822,2018,A1

10
[ 363191-25-7 ]
tert-butyl [(2R)-2-{5-[(4-[1-(3-[tert-butyl(dimethyl)silyl]oxy}propyl)azetidin-3-yl]oxy}phenyl)ethynyl]-1,2-oxazol-3-yl}-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)ethyl]carbamate [ No CAS ]

Reference： [1]Patent: WO2018/216822,2018,A1

11
[ 131543-46-9 ]
[ 76438-34-1 ]
[ 363191-25-7 ]
methyl 3-[(tert-butoxycarbonyl)amino]-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Glyoxal; (S)-2-(tetrahydropyranyloxy)propanal; methyl N³-(tert-butyloxycarbonyl)-(R)-2,3-diaminopropinate In methanol at 20℃; for 0.166667h; Stage #2: With ammonium acetate In methanol at 20℃; for 72h;	29Methyl (2R)-3-[(tert-butoxycarbonyl)amino]-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)propanoate (73) Glyoxal (8.8 mol/L, 4.2 mL) and a solution of methyl 3-[(tert-butoxycarbonyl)amino]-Dalaninate72 (8.0 g, 37 mmol) in MeOH (40 mL) were added to a solution of (2S)-2-[(oxan-2-yl)oxy]propanal (7.5 g, 47 mmol) in MeOH (80 mL). After stirring at room temperature for 10min, ammonium acetate (2.8 g, 36 mmol) was added, and the mixture was stirred at the same temperature for 3 days and concentrated. The residue was purified using column chromatographyon silica gel and eluted with EtOAc/n-hexane to obtain 73 as a mixture of R/S isomers (4.4 g, 30%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.09-6.97 (m, 2 H), 5.59-5.54 (m, 1 H), 5.48-5.41 (m,1 H), 5.12-5.02 (m, 1 H), 4.71-4.65 (m, 1 H), 4.47-4.42 (m, 1 H), 3.95-3.81 (m, 2 H), 3.79-3.71(m, 3 H), 1.87-1.46 (m, 9 H), 1.45-1.36 (m, 9 H). LCMS (ESI) m/z 398 [M+H]+. Rt 0.559 min(Analytical condition B).

Reference： [1]Ushiyama, Fumihito; Takashima, Hajime; Matsuda, Yohei; Ogata, Yuya; Sasamoto, Naoki; Kurimoto-Tsuruta, Risa; Ueki, Kaori; Tanaka-Yamamoto, Nozomi; Endo, Mayumi; Mima, Masashi; Fujita, Kiyoko; Takata, Iichiro; Tsuji, Satoshi; Yamashita, Haruhiro; Okumura, Hirotoshi; Otake, Katsumasa; Sugiyama, Hiroyuki [Bioorganic and Medicinal Chemistry, 2021, vol. 30]

12
[ 363191-25-7 ]
tert-butyl [(2R)-2-[5-(4-[(1R,5S,6s)-3-azabicyclo[3.1.0]hexan-6-yl]ethynyl}phenyl)-1,2-oxazol-3-yl]-2-{2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy}ethyl]-1H-imidazol-1-yl}ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.5 h / 65 °C 7.1: sodium hydroxide / methanol; tetrahydrofuran / 0.33 h / 20 °C
	Multi-step reaction with 6 steps 1.1: ammonium acetate / water; methanol / 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 1.5 h / 60 °C 4.1: potassium carbonate; toluene-4-sulfonic acid / water; methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: trifluoroacetic anhydride; pyridine / chloroform / 1 h / 20 °C / Cooling with ice 6.2: 0.5 h / 65 °C 6.3: 0.33 h / 20 °C

13
[ 363191-25-7 ]
tert-butyl {(2R)-2-{2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy}ethyl]-1H-imidazol-1-yl}-2-[5-(4-[(1R,5S,6s)-3-(trifluoroacetyl)-3-azabicyclo[3.1.0]hexan-6-yl]ethynyl}phenyl)-1,2-oxazol-3-yl]ethyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.5 h / 65 °C

14
[ 363191-25-7 ]
tert-butyl [(2R)-2-{5-[4-({1-[(tert-butoxycarbonyl)amino]cyclopropyl}ethynyl)phenyl]-1,2-oxazol-3-yl}-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: water; ethyl acetate / 0.17 h / 20 °C 3.2: 1 h / 20 °C 3.3: 1 h / 20 °C 4.1: dichloro(1,3-bis(2,6-bis(3-pentyl)phenyl)imidazolin-2-ylidene)(3-chloropyridyl)palladium(II); sodium carbonate / toluene; ethanol / 2 h / 100 °C

15
[ 363191-25-7 ]
tert-butyl [(2R)-2-{5-[4-({3-[(tert-butoxycarbonyl)amino]bicyclo[1.1.1]pentan-1-yl}ethynyl)phenyl]-1,2-oxazol-3-yl}-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: water; ethyl acetate / 0.17 h / 20 °C 3.2: 1 h / 20 °C 3.3: 1 h / 20 °C 4.1: dichloro(1,3-bis(2,6-bis(3-pentyl)phenyl)imidazolin-2-ylidene)(3-chloropyridyl)palladium(II); sodium carbonate / toluene; ethanol / 1 h / 80 °C

16
[ 363191-25-7 ]
tert-butyl [(2R)-2-[5-(4-[(1R,5S,6s)-3-formyl-3-azabicyclo[3.1.0]hexan-6-yl]ethynyl}phenyl)-1,2-oxazol-3-yl]-2-{2-[(1S)-1-hydroxyethyl]-1H-imidazol-1-yl}ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.5 h / 65 °C 7.1: sodium hydroxide / methanol; tetrahydrofuran / 0.33 h / 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C 9.1: tetrahydrofuran / 0.67 h / 20 °C

17
[ 363191-25-7 ]
tert-butyl [(2R)-2-{2-[(1S)-1-hydroxyethyl]-1H-imidazol-1-yl}-2-{5-[4-({(1R,5S,6R)-3-[(2S)-2-hydroxypropyl]-3-azabicyclo[3.1.0]hexan-6-yl}ethynyl)phenyl]-1,2-oxazol-3-yl}ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.5 h / 65 °C 7.1: sodium hydroxide / methanol; tetrahydrofuran / 0.33 h / 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C 9.1: methanol / 2 h / 50 °C / Microwave irradiation

18
[ 363191-25-7 ]
tert-butyl [(2R)-2-[5-(4-[(1r,3R)-3-[tert-butyl(dimethyl)silyl]oxy}cyclobutyl]ethynyl}phenyl)-1,2-oxazol-3-yl]-2-{2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy}ethyl]-1H-imidazol-1-yl}ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: tris(tris[3,5-bis(trifluoromethyl)phenyl]phosphine)palladium; triethylamine; copper(l) iodide / acetonitrile / 0.17 h / 60 °C

19
[ 363191-25-7 ]
tert-butyl [(2R)-2-[5-(4-[(1R,5S,6s)-3-azabicyclo[3.1.0]hexan-6-yl]ethynyl}phenyl)-1,2-oxazol-3-yl]-2-{2-[(1S)-1-hydroxyethyl]-1H-imidazol-1-yl}ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.5 h / 65 °C 7.1: sodium hydroxide / methanol; tetrahydrofuran / 0.33 h / 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

20
[ 363191-25-7 ]
ethyl 4-{(1R,5S,6s)-6-[(4-{3-[(1R)-2-[(tert-butoxycarbonyl)amino]-1-{2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy}ethyl]-1H-imidazol-1-yl}ethyl]-1,2-oxazol-5-yl}phenyl)ethynyl]-3-azabicyclo[3.1.0]hexan-3-yl}butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: tris(tris[3,5-bis(trifluoromethyl)phenyl]phosphine)palladium; triethylamine; copper(l) iodide / acetonitrile / 2 h / 20 °C

21
[ 363191-25-7 ]
ethyl 4-{(1R,5S,6s)-6-[(4-{3-[(1R)-2-[(tert-butoxycarbonyl)amino]-1-{2-[(1S)-1-hydroxyethyl]-1H-imidazol-1-yl}ethyl]-1,2-oxazol-5-yl}phenyl)ethynyl]-3-azabicyclo[3.1.0]hexan-3-yl}butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 6.1: tris(tris[3,5-bis(trifluoromethyl)phenyl]phosphine)palladium; triethylamine; copper(l) iodide / acetonitrile / 2 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C

22
[ 363191-25-7 ]
tert-butyl [3-(hydroxyimino)-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)propyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C

23
[ 363191-25-7 ]
tert-butyl [(2R)-2-[5-(4-iodophenyl)-1,2-oxazol-3-yl]-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C
	Multi-step reaction with 3 steps 1.1: ammonium acetate / water; methanol / 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 1.5 h / 60 °C

24
[ 363191-25-7 ]
tert-butyl {(2R)-2-{2-[(1S)-1-hydroxyethyl]-1H-imidazol-1-yl}-2-[5-(4-iodophenyl)-1,2-oxazol-3-yl]ethyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
	Multi-step reaction with 4 steps 1.1: ammonium acetate / water; methanol / 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 1.5 h / 60 °C 4.1: potassium carbonate; toluene-4-sulfonic acid / water; methanol / 3 h / 20 °C

25
[ 363191-25-7 ]
tert-butyl {(2R)-2-{2-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy}ethyl]-1H-imidazol-1-yl}-2-[5-(4-iodophenyl)-1,2-oxazol-3-yl]ethyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: methanol / 0.17 h / 20 °C 1.2: 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 0.08 h / 62 °C 4.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C
	Multi-step reaction with 5 steps 1.1: ammonium acetate / water; methanol / 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide / chloroform / 1.5 h / 20 °C 3.2: 1.5 h / 60 °C 4.1: potassium carbonate; toluene-4-sulfonic acid / water; methanol / 3 h / 20 °C 5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C

26
[ 363191-25-7 ]
tert-butyl [(2R)-2-(5-iodo-1,2-oxazol-3-yl)-2-(2-{(1S)-1-[(oxan-2-yl)oxy]ethyl}-1H-imidazol-1-yl)ethyl]methylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: ammonium acetate / water; methanol / 72 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 0.25 h / -70 °C 2.2: 16 h / 20 °C 3.1: N-chloro-succinimide; sodium hydrogencarbonate / water; ethyl acetate / 1 h / 20 °C 3.2: 1 h 4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 20 °C

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD. - EP3884940, 2021, A1

27
[ 363191-25-7 ]
C₁₀H₂₀N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethanolamine / dichloromethane / 3.5 h / 0 - 25 °C / Inert atmosphere 2: sodium tetrahydridoborate; lithium chloride / tetrahydrofuran / 2.5 h / 0 - 25 °C

Reference： [1]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - WO2022/36176, 2022, A1

28
[ 363191-25-7 ]
(R)-3-((tert-butoxycarbonyl)amino)-2-((methoxycarbonyl)amino)propyl methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethanolamine / dichloromethane / 3.5 h / 0 - 25 °C / Inert atmosphere 2: sodium tetrahydridoborate; lithium chloride / tetrahydrofuran / 2.5 h / 0 - 25 °C 3: triethanolamine / dichloromethane / 1 h / 0 - 25 °C

Reference： [1]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - WO2022/36176, 2022, A1

29
[ 363191-25-7 ]
C₁₈H₂₃N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethanolamine / dichloromethane / 3.5 h / 0 - 25 °C / Inert atmosphere 2: sodium tetrahydridoborate; lithium chloride / tetrahydrofuran / 2.5 h / 0 - 25 °C 3: triethanolamine / dichloromethane / 1 h / 0 - 25 °C 4: N,N-dimethyl-formamide / 1 h / 60 °C

Reference： [1]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - WO2022/36176, 2022, A1

30
[ 79-22-1 ]
[ 363191-25-7 ]
methyl (R)-3-((tert-butoxycarbonyl)amino)-2-((methoxycarbonyl)amino)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.21 g	With triethanolamine In dichloromethane at 0 - 25℃; for 3.5h; Inert atmosphere;	7.1 Step 1. Preparation of compound SI37, Methyl (R)-3-((tert-butoxycarbonyl)amino)-2- ((methoxycarbonyl)amino)propanoate To a solution of compound SI36 (5.00 g, 22.9 mmol) and TEA (3.64 g, 35.9 mmol, 5.00 mL) in DCM (50.0 mL) at 0 °C under N2 was added methyl chloroformate (2.41 g, 25.5 mmol, 1.98 mL), the mixture was stirred at 25 °C for 3.5 hrs. TLC (Petroleum ether: Ethyl acetate=l:l Rl: Rf= 0.24; Pl: Rf= 0.43) indicated Reactant was consumed completely and one new spot formed. The reaction was clean according to TLC. The reaction was quenched with sat. NaHCCL (50.0 mL), then extract with DCM (20.0 mL*2), the organic phase was dried over Na2SC>4, filtered, concentrated to give a residue. The residue (Petroleum ether: Ethyl acetate=l:l Rl: Rf = 0.24; Pl: Rf = 0.43) was purified by column chromatography (SiCh, Petroleum ether/Ethyl acetate = 5/1 to 1/1). The solution was concentrated to give compound SI37 (3.21 g, 11.6 mmol) as white oil.XH NMR: EC2025-36-P1A1, 400 MHz, CDC13, 35.73 (br s, 1H), 4.88 (br s, 1H),4.32 (br d, 7 = 3.9 Hz, 1H), 3.70 (s, 3H), 3.62 (s, 3H), 3.47 (br s, 2H), 1.36 (s, 9H).
3.21 g	With triethanolamine In dichloromethane at 0 - 25℃; for 3.5h; Inert atmosphere;	7.1 Step 1. Preparation of compound SI37, Methyl (R)-3-((tert-butoxycarbonyl)amino)-2- ((methoxycarbonyl)amino)propanoate To a solution of compound SI36 (5.00 g, 22.9 mmol) and TEA (3.64 g, 35.9 mmol, 5.00 mL) in DCM (50.0 mL) at 0 °C under N2 was added methyl chloroformate (2.41 g, 25.5 mmol, 1.98 mL), the mixture was stirred at 25 °C for 3.5 hrs. TLC (Petroleum ether: Ethyl acetate=l:l Rl: Rf= 0.24; Pl: Rf= 0.43) indicated Reactant was consumed completely and one new spot formed. The reaction was clean according to TLC. The reaction was quenched with sat. NaHCCL (50.0 mL), then extract with DCM (20.0 mL*2), the organic phase was dried over Na2SC>4, filtered, concentrated to give a residue. The residue (Petroleum ether: Ethyl acetate=l:l Rl: Rf = 0.24; Pl: Rf = 0.43) was purified by column chromatography (SiCh, Petroleum ether/Ethyl acetate = 5/1 to 1/1). The solution was concentrated to give compound SI37 (3.21 g, 11.6 mmol) as white oil.XH NMR: EC2025-36-P1A1, 400 MHz, CDC13, 35.73 (br s, 1H), 4.88 (br s, 1H),4.32 (br d, 7 = 3.9 Hz, 1H), 3.70 (s, 3H), 3.62 (s, 3H), 3.47 (br s, 2H), 1.36 (s, 9H).

Reference： [1]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - WO2022/36176, 2022, A1 Location in patent: Paragraph 0143
[2]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - WO2022/36176, 2022, A1 Location in patent: Paragraph 0143

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Ghs Precautionary Statements

Precautionary Statements-General
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P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P264	Wash hands thoroughly after handling.
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P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P320
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P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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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
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P401
P402	Store in a dry place.
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P422
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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. 363191-25-7 ] {[proInfo.proName]}

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[ 363191-25-7 ] Synthesis Path-Upstream 1~2

[ 363191-25-7 ] Synthesis Path-Downstream 1~30

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Amino Acid Derivatives

Precautionary Statements-General

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[ 363191-25-7 ]