[ CAS No. 14907-27-8 ] {[proInfo.proName]}

Name: 14907-27-8|H-D-Trp-OMe.HCl|98%
Brand: Ambeed
SKU: A128314
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Quality Control of [ 14907-27-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 14907-27-8 ]

Product Details of [ 14907-27-8 ]

CAS No. :	14907-27-8	MDL No. :	MFCD00038992
Formula :	C₁₂H₁₅ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XNFNGGQRDXFYMM-HNCPQSOCSA-N
M.W :	254.71	Pubchem ID :	11448200
Synonyms :

Calculated chemistry of [ 14907-27-8 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.25
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	68.64
TPSA :	68.11 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.35
Log Po/w (WLOGP) :	2.01
Log Po/w (MLOGP) :	1.11
Log Po/w (SILICOS-IT) :	2.04
Consensus Log Po/w :	1.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.03
Solubility :	0.239 mg/ml ; 0.000939 mol/l
Class :	Soluble
Log S (Ali) :	-3.42
Solubility :	0.0968 mg/ml ; 0.00038 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.46
Solubility :	0.0881 mg/ml ; 0.000346 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.29

Safety of [ 14907-27-8 ]

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

Application In Synthesis of [ 14907-27-8 ]

* 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 [ 14907-27-8 ]
Downstream synthetic route of [ 14907-27-8 ]

[ 14907-27-8 ] Synthesis Path-Upstream 1~2

1
[ 5619-09-0 ]
[ 7524-52-9 ]
[ 14907-27-8 ]

Reference： [1] Patent: WO2010/148191, 2010, A2, . Location in patent: Page/Page column 45-49; 59

2
[ 14907-27-8 ]
[ 171596-36-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 789 - 792

[ 14907-27-8 ] Synthesis Path-Downstream 1~23

1
[ 14907-27-8 ]
[ 2279-15-4 ]
[ 81444-74-8 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2015 - 2025
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 7177 - 7192

2
[ 14907-27-8 ]
[ 63521-92-6 ]
[ 172946-57-5 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 7920 - 7926

3
[ 14907-27-8 ]
[ 171489-59-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 789 - 792
[2]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 1505 - 1515
[3]Organic Preparations and Procedures International,2005,vol. 37,p. 99 - 102
[4]Synlett,2004,p. 1428 - 1430
[5]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1425 - 1428
[6]Patent: WO2012/107549,2012,A1
[7]Patent: US2013/324730,2013,A1
[8]RSC Advances,2014,vol. 4,p. 1204 - 1211
[9]Patent: WO2016/12539,2016,A1
[10]Patent: CN105384740,2016,A
[11]ACS Chemical Neuroscience,2018,vol. 9,p. 328 - 345
[12]Patent: EP1914235,2008,A1
[13]Patent: WO2009/37556,2009,A1

4
[ 14907-27-8 ]
[ 171596-36-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 789 - 792

5
[ 14907-27-8 ]
[ 171596-29-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 1505 - 1515
[2]Organic Preparations and Procedures International,2005,vol. 37,p. 99 - 102
[3]Synlett,2004,p. 1428 - 1430
[4]Synlett,2004,p. 1428 - 1430
[5]Patent: WO2012/107549,2012,A1
[6]Patent: US2013/324730,2013,A1
[7]RSC Advances,2014,vol. 4,p. 1204 - 1211
[8]Patent: WO2016/12539,2016,A1
[9]Patent: CN105541835,2016,A
[10]Patent: CN105384740,2016,A
[11]Patent: CN106810554,2017,A
[12]Patent: CN106810554,2017,A

6
[ 14907-27-8 ]
[ 24332-20-5 ]
C₁₅H₁₈N₂O₃ [ No CAS ]
[ 406950-18-3 ]

Yield	Reaction Conditions	Operation in experiment
32%		A mixture of D-tryptophan methyl ester hydrochloride (1.27 g, 5.00 mmol), <strong>[24332-20-5]methoxyacetaldehyde dimethyl acetal</strong> (0.80 mL, 6.2 mmol) in isopropyl alcohol (12 mL) and water (2 mL) was stirred at 60 C. under a nitrogen blanket for 20 minutes. To the resulting clear solution was added 2N HCl (1 mL), and the resulting yellow solution stirred at 60 C. for 1 hour. The solution then was cooled to room temperature, diluted with ethyl acetate (100 mL), and neutralized with saturated aqueous sodium bicarbonate (NaHCO3) (20 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate (Na2SO4), filtered, and the solvent was removed under reduced pressure to provide a yellow solid. The residue was purified by column chromatography, eluting with methylene chloride:ethyl acetate (4:1), to provide the (+)-cis carboline Intermediate 12 as a white solid (435 mg, 32%): TLC Rf (4:1 methylene chloride/ethyl acetate)=0.28; 1H NMR (300 MHz, CDCl3): delta: 8.48 (bs, 1H), 7.50 (d, J=8.0 Hz, 1H), 7.34 (d, J=8.0 Hz, 1H), 7.20-7.03 (m, 2H), 4.42-4.34 (m, 1H), 3.87-3.54 (m, 6H), 3.50 (s, 3H), 3.20-3.10 (m, 1H), 2.90-2.76 (m, 1H). The trans carboline was incompletely eluted from the column: TLC Rf (4:1 methylene chloride/ethyl acetate)=0.19.

Reference： [1]Patent: US2003/236263,2003,A1 .Location in patent: Page 15

7
[ 127657-97-0 ]
[ 14907-27-8 ]
[ 406950-20-7 ]

Yield	Reaction Conditions	Operation in experiment
27%	With hydrogenchloride; In water; isopropyl alcohol; at 70℃; for 18h;	D-tryptophan methyl ester hydrochloride (4.07 g, 16 mmol) and Intermediate 14 (3.75 g, 19 mmol) were combined with stirring in a solution of IPA (80 mL) and water (20 mL). To the resulting mixture was added 2N HCl (2 mL) and the resulting mixture heated at 70 C. for 18 hours. The mixture was neutralized with saturated aqueous NaHCO3, then extracted with methylene chloride (2×400 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with methylene chloride/acetone (98:2), to provide the cis-carboline Intermediate 15 as an orange oil (1.5 g, 27%): TLC Rf (6:1 methylene chloride/ethyl acetate)=0.49; 1H NMR (300 MHz, CDCl3): delta: 8.46 (s, 1H), 7.50.(d, J=0.7 Hz, 1H), 7.47-7.25 (m, 6H), 7.18-7.06 (m, 2H), 4.65 (s, 2H), 4.44-4.39 (m, 2H), 3.88-3.82 (m, 1H), 3.81 (s, 3H), 3.66 (t, J=8.7 Hz, 1H), 3.18-3.11 (m, 1H), 2.88-2.78 (m, 1H), 1.87 (bs, 1H).

Reference： [1]Patent: US2003/236263,2003,A1 .Location in patent: Page 16

8
[ 14907-27-8 ]
[ 88050-17-3 ]
C₃₂H₃₁N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃;	To a mixture of N-9-fluorenylmethoxycarbonyl-L-trans-4-hydroxyproline (10.2 g), D-tryptophan methyl ester hydrochloride (8.1 g), and benzotriazol-1-yloxy- tris (pyrrolidino)-phosphonium hexafluorophosphate (15 g) in acetonitrile (200 mL) was added diisopropylethylamine (15 mL), at 0C. The resulting mixture was stirred overnight at room temperature. The solvent was removed in vacuo, dissolved in ethyl acetate and extracted twice with water and twice with 2 M hydrochloric acid. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was dissolved in acetonitrile (200 mL) and piperidine (25 mL) was added, after 2 hours at room temperature the formed 1- (9H-Fluoren-9-ylmethyl)-piperidine was removed by filtration and the remaining solution was left for 72 hours. The formed crystalline material was collected by filtration to afford (3R, 7R, 8aS)-7-hydroxy-3- (1 H- indol-3-ylmethyl)-hexahydro-pyrrolo [1,2-a] pyrazine-1, 4-dione (7.4 g) (intermediate 6).

Reference： [1]Patent: WO2003/84955,2003,A1 .Location in patent: Page/Page column 11-12

9
[ 14907-27-8 ]
[ 56059-30-4 ]
[ 1204404-91-0 ]

Reference： [1]Molecules,2009,vol. 14,p. 3142 - 3152

10
[ 73960-07-3 ]
[ 14907-27-8 ]
[ 1018815-60-5 ]
(1S,3R)-1-(4-difluoromethoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1274 - 1286

11
[ 73960-07-3 ]
[ 14907-27-8 ]
[ 1018815-61-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1274 - 1286

12
[ 14907-27-8 ]
[ 32863-33-5 ]
[ 76-05-1 ]
[ 1356345-79-3 ]
(1S,3R)-1-benzo[1,2,5]oxadiazol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester trifluoroacetate salt [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1274 - 1286

13
[ 120-57-0 ]
[ 14907-27-8 ]
[ 171596-29-5 ]

Reference： [1]Patent: WO2012/107549,2012,A1

14
[ 120-57-0 ]
[ 14907-27-8 ]
[ 79-04-9 ]
[ 171489-59-1 ]

Yield	Reaction Conditions	Operation in experiment
86%		59 g (0.39 mol) of piperonal (2) and 25 (0.098 mol) g of D-tryptophan methyl ester hydrochloride (1 HCI) were added to a reactor. The mixture was heated to 85C and stirred at this temperature for 3 h. It was allowed to cool to 55- 60C. 160 ml of THF, 40 ml of water and 41 ml (mol) of TEA were added. It was stirred at 55-60C until complete dissolution. It was cooled to 0-10C and 14 ml of chloroacetyl chloride (0.17 mol) were added dropwise, dissolved in 15 ml of THF. It was stirred at 0-10C for 1 h. 150 ml of the mixture were distilled at a Tmax of 45C. 240 ml of IPA and 60 ml of water were added. 50 ml of the mixture were distilled at a Tmax of 45C. It was cooled to room temperature stirred for 2 h at said temperature. The precipitates obtained was filtered and washed with IPA and dried under vacuum at 50C. This produced 36 g of 5cis (86% yield). HPLC Purity: 97.4%.

Reference： [1]Patent: WO2012/107549,2012,A1 .Location in patent: Page/Page column 12

15
[ 14907-27-8 ]
[ 35737-15-6 ]
Fmoc-D-Trp-D-Trp-OMe [ No CAS ]

Reference： [1]ChemPhysChem,2012,vol. 13,p. 2748 - 2760

16
[ 28785-06-0 ]
[ 14907-27-8 ]
[ 1417796-76-9 ]
[ 1417796-77-0 ]

Reference： [1]Journal of Chemical Information and Modeling,2013,vol. 53,p. 176 - 187

17
[ 14907-27-8 ]
[ 249921-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 38 °C / Inert atmosphere; Large scale 2.1: sodium hydroxide / water; tert-butyl methyl ether / 20 °C / Large scale 3.1: 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 3.2: 20 °C 4.1: hydrogenchloride / ethyl acetate
	Multi-step reaction with 4 steps 1: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 38 °C / Inert atmosphere; Large scale 2: sodium hydroxide / water; tert-butyl methyl ether / 20 °C / Large scale 3: triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 25 °C / Inert atmosphere 4: hydrogenchloride / ethyl acetate

Reference： [1]Paul, Bernhard J.; Littler, Benjamin J.; Jos, Frederic; Vogt, Paul F.; Pines, Seemon H. [Organic Process Research and Development, 2006, vol. 10, # 2, p. 339 - 345]
[2]Paul, Bernhard J.; Littler, Benjamin J.; Jos, Frederic; Vogt, Paul F.; Pines, Seemon H. [Organic Process Research and Development, 2006, vol. 10, # 2, p. 339 - 345]

18
[ 23911-25-3 ]
[ 14907-27-8 ]
EDTA-bis(L-triptophan methyl ester) [ No CAS ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2014,vol. 640,p. 1095 - 1101

19
[ 14907-27-8 ]
[ 1397-89-3 ]
amphotericin B N-(D)-methoxytryptophanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.85%	With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl acetamide; at 20℃;	Example 7 Synthesis of Amide 7: N-(D)-tryptophanamide of AmB In another preferred embodiment the invention provides the AmB analogue denominated amide 7: N-(D)-tryptophanamide of AmB, represented by formula VII; using D-tryptophan as the starting amine. Fort this derivative the same structural aspects of the synthesis of amide 6 were taken into account and it was observed in its synthesis the possible effect on the antibiotic activity that has the change in the stereochemistry of this derivative regarding amide 6. For L-tryptophan and D-tryptophan, before the amide synthesis, it was necessary to perform the sterification reaction of the carboxylic acid to protect it in form of hydrochloride of the methyl ester of tryptophan. This synthesis was performed by reacting 1 equivalent of the amino acid L-tryptophan or D-tryptophan (L-Trp or D-Trp) with excess MeOH and 2 equivalents of Me3SiCl to procure the white precipitate of the hydrochloride of the methyl ester of L-tryptophan or D-tryptophan. Scheme 6 shows the reaction mechanism proposed for this synthesis. The first step in the reaction consists of the nucleophilic addition of the tryptophan carboxyl function (E) on the Si of Me3SiCl (F) inducing the displacement of the Cl- ion. The silicon esters (intermediates G and H) are in an equilibrium in which it is proposed that the deprotonated form is more susceptible to the nucleophilic addition of MeOH. This will form the hydrochloride of the methyl ester tryptophan with trymethylsilanol as a byproduct of the reaction. The hydrochloride of the tryptophan methyl ester is used for the synthesis of the amides of AmB incorporating only an excess of Et3N as basic reagent in the method of Jarzebski. This liberates the form of the methyl ester of the tryptophan to act as amine in the reaction. It is reported that by incorporating the tryptophan structure in AmB polyene molecules they fluoresce under UV light. The tryptophan methyl ester was used for the synthesis of AmB amides as a means to procure amides that fluoresce under UV light. This is a desirable characteristic for experiments of electrophysiology in unit channel as because of this, the channels would present this type of fluorescence. Characterization of Amide N-(D)-tryptophanamide of AmB. The IR spectrum of the product is almost identical to that of amide 6, showing only slight differences in the intensity of the signals. The derivative had a value of Rf=0.62 for which it is qualitatively considered that this product is non-polar regarding AmB. These two results help confirm that amide 7 has the same structure of amide 6, and its epimer. During the process of purification of amide 7 two products were isolated: amide 7a and amide 7b. The IR spectra of both amides have a similar difference to that of amide 2a and amide 2b in the absorption band of the polyhydroxylated chain. Here the difference in the intensity of the bands is not too large. Because of this it is believed that this is the same structure, and it is supposed that the solvation with ether (of the purification) occurred in the polyhydroxylated chain for the amide 7b. Moreover, it is likely that the antibiotic behavior is diminished because the actual concentration of the derivative could be less than that contemplated in the preparation of the amide solution. It is noteworthy that the rest of the spectra of both products are the same. Here, being the epimer (D) of the N-(L)-tryptophanamide, the same values of the derivative 6 are contemplated. Therefore, this synthesis is to determine whether the difference the epimers (L)-(D) stereochemistry will affect the antibiotic activity.

Reference： [1]Patent: US2014/256663,2014,A1 .Location in patent: Paragraph 0145-0151

20
[ 1917-15-3 ]
[ 14907-27-8 ]
(R)-methyl (5-methylfuran-2-carbonyl)tryptophanate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: Furan-2-carboxylic acid, thiophene-2-carboxylic acid, 5-methylthiophene-2-carboxylic acid, benzofuran-2-carboxylic acid, benzothiophene-2-carboxylic acid, and amino acid ester hydrochlorides were obtained from commercial supplies and were used without further purification. To a two?necked flask, an amino acid ester hydrochloride (1.1 mmol), 1?ethyl?3?dimethylaminopropylcarbodiimide hydrochloride (EDC, 0.29 g, 1.5 mmol), HOBt (0.20 g, 1.5 mmol), Et3N (0.42 mL, 3.0 mmol), and CHCl3 or DMF (2.2 mL) were added, and the mixture was stirred at 0 °C for 10 min. Furan-2-carboxylic acid or thiophene-2-carboxylic acid dissolved in DMF (2.2 mL) was added, and then stirred for 17 h. The reaction mixture was diluted with water and extracted with EtOAc (3 x 20 mL). The organic phase was then washed with 3 N HCl aq. (3 x 20 mL), saturated NaHCO3 aq. (3 x 20 mL), and brine (20 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/EtOAc = 1/1) to obtain the product. The purity of the product was confirmed by 1H-NMR. Stereochemistry of the final product was measured by high-performance liquid chromatography (HPLC) with a chiral column (Compound 16). The chart is shown in the supporting information.

Reference： [1]Molecules,2018,vol. 23

21
[ 14907-27-8 ]
[ 1219810-16-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine / benzene / 1 h / 20 °C 2.1: trifluoroacetic acid / benzene / 1 h / Heating / reflux; Molecular sieve 3.1: trifluoroacetic acid / benzene / 3 h / 20 °C / Heating / reflux; Molecular sieve 3.2: pH 8 4.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: triethylamine / toluene / 18 h / 20 °C 1.2: 4 h / 120 °C / Molecular sieve 2.1: sodium hydrogencarbonate / chloroform / 4 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK - WO2008/103470, 2008, A2
[2]Current Patent Assignee: FERRO THERAPEUTICS INC - US2019/263802, 2019, A1

22
[ 2130-96-3 ]
[ 14907-27-8 ]
[ 2789-92-6 ]
(1S,4R)-4-((1H-indol-3-yl)methyl)-1-(4-(benzyloxy)benzyl)-8,10-dichloro-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3,6(4H)-dione [ No CAS ]
4-((1H-indol-3-yl)methyl)-1-(4-(benzyloxy)benzyl)-8,10-dichloro-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3,6(4H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		In a closed vial 3,5-dichloro anthranilic acid (xiii, 41 mg, 200 mol), N-Boc-o-Bn-Tyrosine (xii,74 mg, 200 mol), and triphenylphosphite (63 muL, 220 mol) were added along with 1 mL of driedpyridine. The vial was heated in heating block with stirring at 55 C for 16-24 h. After cooling themixture to room temperature, D-tryptophan methyl ester hydrochloride (ii, 51 mg, 200 mol) wasadded, and the mixture was irradiated in the microwave at the constant temperature at 220 C for1.5 min. Reaction mixtures were prepared in the same conditions and treated in parallel. After removingthe solvent with toluene, the crude product was purified by flash column chromatography usinghexane: EtOAc (60:40) as a mobile phase. The preparative TLC was performed using CH2Cl2:Me2CO(95:5) as mobile phase. The major compound appeared as a black spot with no fluorescence underthe UV light (366 nm). Compound 12 was collected as orange solids. Before analysis, compound wasrecrystallized from methanol. Yield: 26.2 mg, 2.2%; er 67:33; m.p.: 233-235 C; [alpha]30D = +244.44 (c 0.045;CH3OH); max (KBr) 3424, 3334, 2921, 1681, 1593, 1511, 1455, 1247,1012, 695, and 420 cm1; 1H NMR(300 MHz, CDCl3): delta 8.26 (d, 1H, J = 2.4 Hz, CH), 8.09 (br, 1H, NH-Trp), 7.85 (d, 1H, J = 2.4 Hz, CH),7.44 (dd, 5H, J = 6.4 and 2.0 Hz, CH-Bz), 7.39 (d, 2H, J = 8.2 Hz, CH-Trp), 7.19 (t, 1H, J = 7.7 Hz, CH-Trp),6.96 (t, 1H, J = 7.5 Hz, CH-Trp), 6.75 (d, 2H, J = 8.7 Hz, CH-Tyr), 6.62 (d, 1H, J = 2.3 Hz, CH-Trp), 6.40(d, 2H, J = 8.5 Hz, CH-Tyr), 5.56 (dd, 1H, J = 5.2 and 2.6, CH-Trp), 5.41 (s, 1H, NH-amide), 5.06 (s, 2H,CH2-Bz), 3.77 (dd, 1H, J = 15.0 and 2.6 Hz, CH2-Trp), 3.62 (dd, 1H, J = 15.6 and 4.1 Hz, CH2-Trp), 3.50(dd, 1H, J = 17.5 and 4.4 Hz, CH2-Tyr), 2.95 (dd, J = 10.8 and 3.6 Hz, CH-Tyr), 2.51 (dd, 1H, J = 14.8 and10.9 Hz, CH2-Tyr); 13C NMR (75 MHz, CDCl3): delta 168.7 (C=O), 159.2 (C=O), 158.0 (C-Tyr), 152.0 (C=N),142.4 (C), 136.9 (C-Bz), 136.1(C-Trp), 135.1 (CH), 133.2 (C-Cl), 132.6 (C-Cl), 129.6 (CH-Tyr (2)), 128.7(CH-Bz (2)), 128.1 (CH-Bz), 127.4 (CH-Bz(2)), 126.9 (C-Trp), 126.6 (C-Tyr), 125.2 (CH), 123.7 (CH-Trp),122.9 (CH-Trp), 122.4 (C), 118.9 (CH-Trp), 115.5 (CH-Tyr (2H)), 111.2 (CH-Trp), 109.4 (C-Trp), 70.1(CH2-Bz), 57.6 (CH-Trp), 53.1 (CH-Tyr), 36.9 (CH2-Tyr), 27.1 (CH2-Trp). (+)-HRMS-ESI m/z 609.1427(M + H)+, (calculated for C34H27N4O3Cl2, 608.1382).

Reference： [1]Molecules,2019,vol. 24

23
[ 14907-27-8 ]
[ 1405-86-3 ]
3-O-{2-O-[N-(β-D-glucopyranosyluronoyl)-D-tryptophan methyl ester]-N-(β-D-glucopyranosyluronoyl)-D-tryptophan methyl ester}-(3β,20β)-11-oxo-30-(N-carbonyl-D-tryptophan methyl ester)-30-norolean-12-ene [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
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.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
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. 14907-27-8 ] {[proInfo.proName]}

Quality Control of [ 14907-27-8 ]

Related Doc. of [ 14907-27-8 ]

Product Details of [ 14907-27-8 ]

Calculated chemistry of [ 14907-27-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 14907-27-8 ]

Application In Synthesis of [ 14907-27-8 ]

[ 14907-27-8 ] Synthesis Path-Upstream 1~2

[ 14907-27-8 ] Synthesis Path-Downstream 1~23

Pharmaceutical Intermediates of [ 14907-27-8 ]

Anamorelin Related Intermediates

Related Functional Groups of [ 14907-27-8 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 14907-27-8 ]

Related Functional Groups of
[ 14907-27-8 ]