[ CAS No. 111524-95-9 ] {[proInfo.proName]}

Name: 111524-95-9|Fmoc-D-Phg-OH|98%
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Quality Control of [ 111524-95-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 111524-95-9 ]

SDS Specification

Alternatived Products of [ 111524-95-9 ]

Product Details of [ 111524-95-9 ]

CAS No. :	111524-95-9	MDL No. :	MFCD00190891
Formula :	C₂₃H₁₉NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PCJHOCNJLMFYCV-OAQYLSRUSA-N
M.W :	373.40	Pubchem ID :	2756108
Synonyms :	(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid

Calculated chemistry of [ 111524-95-9 ]

Physicochemical Properties

Num. heavy atoms :	28
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.13
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	104.85
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	4.35
Log Po/w (WLOGP) :	4.03
Log Po/w (MLOGP) :	3.21
Log Po/w (SILICOS-IT) :	3.64
Consensus Log Po/w :	3.49

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-4.91
Solubility :	0.0046 mg/ml ; 0.0000123 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.65
Solubility :	0.000829 mg/ml ; 0.00000222 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.98
Solubility :	0.0000387 mg/ml ; 0.000000104 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.78

Safety of [ 111524-95-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335-H413	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 111524-95-9 ]

* 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 [ 111524-95-9 ]
Downstream synthetic route of [ 111524-95-9 ]

[ 111524-95-9 ] Synthesis Path-Upstream 1~4

1
[ 470670-74-7 ]
[ 111524-95-9 ]

Reference： [1] Organic Letters, 2002, vol. 4, # 19, p. 3321 - 3324

2
[ 875-74-1 ]
[ 82911-69-1 ]
[ 111524-95-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4818 - 4839

3
[ 111524-95-9 ]
[ 220498-02-2 ]

Reference： [1] Synthesis, 1998, # 6, p. 837 - 841

4
[ 111524-95-9 ]
[ 209252-15-3 ]

Reference： [1] Synthetic Communications, 2002, vol. 32, # 4, p. 651 - 657
[2] Synthesis, 1998, # 6, p. 837 - 841

[ 111524-95-9 ] Synthesis Path-Downstream 1~88

1
[ 111524-95-9 ]
[ 111524-97-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 3,3-dichloro-1,2-diphenylcyclopropene; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - 20℃; for 0.166667h;	General procedure: To a solution of 3,3-dichloro-1,2-diphenylcyclopropene at -10 oC [1.1 equiv. prepared by adding diphenylcyclopropenone (1.0 equiv.) in DCM and oxalyl chloride (1.0 equiv.) at rt and stirred until the gas evolution has ceased] was added a solution of Nalpha-protected amino acid (1.0 equiv.) and diisopropylethylamine (1.2 equiv.) in dichloromethane and stirred. After 10 min hydroxylamine hydrochloride (NH2OH.HCl, 1.5 equiv.) in methanolic potassium hydroxide was added to the reaction mixture and stirred of another 45 min. The solvent was removed under reduced pressure; the residue obtained was diluted with EtOAc, washed with 10% citric acid solution, water and brine solution. The organic phase was dried over anhydrous Na2SO4 and removed under reduced pressure. The crude residue was purified by column chromatography using n-hexane and ethyl acetate as eluents.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 394 - 396
[2]Journal of Organic Chemistry,1988,vol. 53,p. 875 - 878
[3]Journal of the Chemical Society. Perkin transactions I,2000,p. 4328 - 4331
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2009,vol. 48,p. 981 - 988
[5]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6327 - 6330
[6]Arkivoc,2018,vol. 2018,p. 449 - 457

2
[ 111524-95-9 ]
[ 543-27-1 ]
C₂₈H₂₇NO₆ [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2004,vol. 43,p. 1282 - 1287
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2009,vol. 48,p. 574 - 579

3
[ 629672-19-1 ]
[ 111524-95-9 ]
2-(4-fluoro-3-methyl-benzenesulfonylamino)-N-hydroxy-2-phenyl-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 964 - 968

4
(R)-allyl-(N-9-fluorenylmethoxycarbonyl)phenylglycinate [ No CAS ]
[ 111524-95-9 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 3321 - 3324

5
[ 7364-51-4 ]
[ 111524-95-9 ]
[ 852866-05-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2006,vol. 45,p. 1880 - 1886

6
[ 111524-95-9 ]
Fmoc-D-Phg-NH₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7038 - 7041

7
[ 111524-95-9 ]
[ 329309-03-7 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 9804 - 9807
[2]Journal of the Chemical Society. Perkin transactions I,2000,p. 4328 - 4331

8
[ 111524-95-9 ]
[ 852866-05-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2004,vol. 43,p. 1282 - 1287

9
[ 470670-74-7 ]
[ 111524-95-9 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 3321 - 3324

10
[ 111524-95-9 ]
[ 209252-15-3 ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 651 - 657
[2]Synthesis,1998,p. 837 - 841

11
[ 111524-95-9 ]
[ 111524-87-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,2000,p. 4328 - 4331
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 394 - 396
[3]Journal of Organic Chemistry,1988,vol. 53,p. 875 - 878

12
[ 111524-95-9 ]
(3-Diazo-2-oxo-1-phenyl-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]

Reference： [1]Synthesis,1998,p. 837 - 841

13
[ 111524-95-9 ]
[ 111524-94-8 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 875 - 878

14
[ 111524-95-9 ]
[ 94778-64-0 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 875 - 878

15
[ 111524-95-9 ]
[ 215178-43-1 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5260 - 5266

16
H-Gly-2-chlorotrityl resin [ No CAS ]
[ 111524-95-9 ]
Fmoc-D-Tyr(O-tBu)-OH [ No CAS ]
N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine [ No CAS ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₅₅H₆₈N₈O₁₀S [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3805 - 3809

17
[ 1315054-15-9 ]
[ 111524-95-9 ]
[ 1233241-45-6 ]

Reference： [1]Synlett,2010,p. 1096 - 1100

18
[ 111524-95-9 ]
[ 1359870-36-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of acid (1.0 mmol) and T3P (1.2 mmol) in dry CH3CN (8.0 mL) was added Et3 N (1.5 mmol) at 0 C followed by the finely ground Na2S (3.0 mmol) and the reaction mixture was stirred for 2 to 3 h till the completion of reaction as monitored by TLC. Then the reaction mixture was concentrated and then diluted with water. The resultant solution was then acidified with citric acid solution (10%) and the product was extracted into EtOAc (10 mL). The organic layer was washed with water (2 × 10 mL), brine (10 mL) and dried over anhydrous Na2SO4. Solvent was evaporated in vacuo to obtain aminothioacid in a quantitative yield.Method for HPLC analysis: Gradient 0.1% TFA, water/acetonitrile (30:70) in 30 min with a flow rate of 0.5 ml/min. lambda = 254 nm (Fmoc, Z), 211 nm (Boc).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1406 - 1409

19
[ 2577-90-4 ]
[ 111524-95-9 ]
(S)-methyl 2-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-phenylethaneselenoamido)-3-phenylpropanoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 2689 - 2702

20
[ 2577-90-4 ]
[ 111524-95-9 ]
[ 111524-87-9 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 2689 - 2702

21
[ 135776-98-6 ]
[ 111524-95-9 ]
[ 1417604-08-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

22
[ 111524-95-9 ]
[ 1417603-94-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

23
[ 111524-95-9 ]
C₃₈H₃₀N₂O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

24
[ 111524-95-9 ]
[ 1417604-13-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

25
[ 111524-95-9 ]
[ 1417604-14-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

26
[ 111524-95-9 ]
[ 1417603-98-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

27
[ 111524-95-9 ]
[ 1417603-99-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

28
[ 111524-95-9 ]
[ 1417603-81-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

29
[ 111524-95-9 ]
[ 1417603-82-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 85 - 89

30
[ 1453473-29-4 ]
[ 35661-40-6 ]
[ 111524-95-9 ]
[ 1453474-63-9 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

31
[ 1453473-29-4 ]
[ 111524-95-9 ]
[ 1453474-62-8 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

32
Fmoc-Tyr(Clt)-OH [ No CAS ]
[ 1453473-29-4 ]
[ 111524-95-9 ]
[ 1453474-64-0 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

33
[ 1453473-29-4 ]
[ 111524-95-9 ]
[ 143824-78-6 ]
[ 1453474-65-1 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

34
[ 1453473-29-4 ]
[ 111524-95-9 ]
N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine [ No CAS ]
[ 1453474-66-2 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

35
[ 1453473-52-3 ]
[ 35661-40-6 ]
[ 111524-95-9 ]
[ 1453474-38-8 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

36
[ 1453473-52-3 ]
[ 111524-95-9 ]
[ 1453474-37-7 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

37
Fmoc-Tyr(Clt)-OH [ No CAS ]
[ 1453473-52-3 ]
[ 111524-95-9 ]
[ 1453474-39-9 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

38
[ 1453473-52-3 ]
[ 111524-95-9 ]
[ 143824-78-6 ]
[ 1453474-40-2 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

39
[ 1453473-52-3 ]
[ 111524-95-9 ]
N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine [ No CAS ]
[ 1453474-41-3 ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 82 - 94

40
[ 111524-95-9 ]
nystatin [ No CAS ]
[ 1454835-92-7 ]

Yield	Reaction Conditions	Operation in experiment
92 mg		Example 7. Synthesis of N-aminoacyl and N-(N'-alkylamino)acyl derivatives of Nystatin 0,26 mmol of N-(9-fluorenylomethoxycarbonyl)aminoacid (Fmoc-aminoacid), 0,26 mmol of N-hydroxysuccinimide (HONSu), 53 mg (0,26 mmol) of dicyclohexylcarbodiimide (DCC) is dissolved in 3 ml of dimethyl formamide (DMF) in 50 ml round-bottomed flask equipped with a magnetic stirrer. The reaction mixture is stirred at 37 C for 1 hour. The reaction progress is monitored by thin layer chromatography (TLC) on Silica Gel (60 F254, Merck) in ethyl aceteate:hexan (7:3 v/v) solvent system. During the reaction, the precipitated N,N- dicyclohexylurea is filtered and washed with 1 ml of DMF. To the filtrate 200 mg (0.22 mmol) of Nystatin Ai and 0.04 ml (0.22 mmol) of triethylamine (TEA) are added. Stirring is continued at 37 C for 3 hours. After the reaction, another portion of 0.04 ml (0.22 mmol) of TEA is added and the reaction mixture is left for 2 hours at room temperature, and then added dropwise to 150 ml of diethyl ether. The resulting, pale yellow precipitate, is filtered under reduced pressure on a Millipore funnel. The crude product is washed twice with diethyl ether (2x50 ml) and then dried in a vacuum desiccators. The residue is purified on column chromatography on normal phase, where the solid phase is Silica Gel and solvent system is chloroform: methanol: water (15:8: 1 v/v). The fractions with pure product were collected and combined, then evaporated under reduced pressure at temperature not exceeding 35 C. The following derivatives of Nystatin Ai are obtained in the reaction of the corresponding protected amino acids: a) In the reaction with N-Fmoc-Z)-phenylglycine is obtained 92 mg of N-D- phenylglycylnystatin Ai (N33) TLC Rf= 0,38; UV-vis: lambdaomegaalphachi (MeOH) 319; 304; 291 nm; (MeOH, lambda = 304 nm) = 610 (theoretically for C55H82 2O18 is 691); MS-ESI calculated for C55H82 2O18 [M+H]+:1059,6; found 1059,6.

Reference： [1]Patent: WO2013/132014,2013,A1 .Location in patent: Page/Page column 40

41
C₄₂H₄₀NO₆Pol [ No CAS ]
[ 111524-95-9 ]
[ 1598415-97-4 ]
[ 1598416-10-4 ]
[ 1598416-11-5 ]
[ 1598416-12-6 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2454 - 2457

42
[ 19533-98-3 ]
[ 111524-95-9 ]
[ 1575689-22-3 ]

Yield	Reaction Conditions	Operation in experiment
54.03%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 3h;	Methyl 2alpha-O-(N-Fluorenonemethyoxycarbonyl)-phenyglycylurs-3beta,23-isopropylidenedioxyurs-12-ene-28-oate(A-4) A solution of A-2 (530 mg, 0.98 mmol) and Fmoc-Dphenylglycine(550 mg, 1.46 mmol) in dry dichloromethane(8 mL) was added 4-dimethylamiopryidine (0.18 g,1.46 mmol) and stirred. Dropwise the solution of 1-ethyl-3-(3-dimethyllaminopropyl) carbodiimide hydrochloride (560 mg,1.46 mmol) in dry dichloromethane (8 mL) to reaction mixtureat 0C. Stirring the reaction mixture for 5 min at 0C. Keepstirring the reaction mixture for 3 h at room temperature. Thereaction mixture was diluted with dichloromethane (50 mL)and washed with water (30 mL×3) and saturated NaCl solution(10 mL). The organic layer was dried over anhydrous magnesiumsulfate. Filtration and evaporation of solvent at reducedpressure gave light yellow solid, which was purified by silicagel chromatography with a gradient elution of ethyl acetate-petrol ether (1 : 5, v/v) to afford a white solid 0.47 g, 54.03%,mp 88.2-88.5C; 1H-NMR (400 MHz, CDCl3) delta: 7.69 (d,J=7.5 Hz, 2H, fluorenyl H-4, H-5), 7.51 (d, J=6.9 Hz, 2H, fluorenylH-1, H-8), 7.32 (d, J=7.4 Hz, 2H, fluorenyl H-3, H-6),7.26 (d, J=5.2 Hz, 2H, fluorenyl H-2, H-7), 7.34-7.21 (m, 5H,Ph-H), 5.82 (d, J=7.2 Hz, 1H, Ph-CH), 5.26 (d, J=7.4 Hz, 1H,-NH), 5.18 (s, 1H, H-12), 5.10-5.08 (m, 1H, H-2), 4.34-4.30 (m, 2H, -CH2-O), 4.15 (t, J=7.0 Hz, 1H, fluorenyl H-9),3.53 (s, 3H, -OCH3), 3.39 (d, J=10.7 Hz, 1H, H-3), 3.29 (t,J=10.4 Hz, 2H, H-23), 2.16 (d, J=10.9 Hz, 1H, H-18), 1.01(s, 9H, =C(CH3)2, -CH3), 1.12, 0.92, 0.65 (each, 3H), 0.88(d, J=5.3 Hz, 1H, H-29), 0.79 (d, J=6.5 Hz, 1H, H-30); IRnumax (KBr, cm-1): 3436, 2924, 2851, 1719, 1501, 1449, 1380,1198; ESI-MS: m/z 898.4 [M-H]-.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 5.08h;	General procedure: A solution of compound 3 (400 mg, 0.86 mmol) and <strong>[111524-95-9]Fmoc-D-phenylglycine</strong> (382 mg, 1.02 mmol) in dry methylene chloride (7 mL) was added to 4-dimethylaminopyridine (124 mg, 1.02 mmol) and stirred. A solution of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (197 mg, 1.02 mmol in dry dichloromethane (3 mL)) was added drop-wise to the reaction mixture at 0C and the mixture was stirred for 5 min at 0C, followed by additional stirring for 5 h at room temperature. The reaction mixture was then diluted with methylene chloride (50 mL) and washed with water (15 mL×3) and saturated sodium chloride solution (30 mL). The organic layer was dried over anhydrous magnesium sulfate. The residue was filtered, the remaining solvent was removed by evaporation at reduced pressure, and the isolated material was purified by silica gel chromatography with a gradient elution of ethyl acetate-petrol ether (1 : 10, v/v) and the obtained white solid was recrystallized from methanol, providing 3a(410 mg, 58.1%) as colorless solid

Reference： [1]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 1015 - 1023
[2]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 764 - 771

43
nystatin A1 [ No CAS ]
[ 111524-95-9 ]
N-D-phenylglycylnystatin A1 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92 mg		0.26 mmol of N-(9-fluorenylomethoxycarbonyl)aminoacid (Fmoc-aminoacid), 0.26 mmol of N-hydroxysuccinimide (HONSu), 53 mg (0.26 mmol) of dicyclohexylcarbodiimide (DCC) is dissolved in 3 ml of dimethyl formamide (DMF) in 50 ml round-bottomed flask equipped with a magnetic stirrer. The reaction mixture is stirred at 37 C. for 1 hour. The reaction progress is monitored by thin layer chromatography (TLC) on Silica Gel (60 F254, Merck) in ethyl aceteate: hexan (7:3 v/v) solvent system. During the reaction, the precipitated N,N-dicyclohexylurea is filtered and washed with 1 ml of DMF. To the filtrate 200 mg (0.22 mmol) of Nystatin A1 and 0.04 ml (0.22 mmol) of triethylamine (TEA) are added. Stirring is continued at 37 C. for 3 hours. After the reaction, another portion of 0.04 ml (0.22 mmol) of TEA is added and the reaction mixture is left for 2 hours at room temperature, and then added dropwise to 150 ml of diethyl ether. The resulting, pale yellow precipitate, is filtered under reduced pressure on a Millipore funnel. The crude product is washed twice with diethyl ether (2×50 ml) and then dried in a vacuum desiccators. The residue is purified on column chromatography on normal phase, where the solid phase is Silica Gel and solvent system is chloroform:methanol:water (15:8:1 v/v). The fractions with pure product were collected and combined, then evaporated under reduced pressure at temperature not exceeding 35 C. The following derivatives of Nystatin A1 are obtained in the reaction of the corresponding protected amino acids:

Reference： [1]Patent: US2015/45316,2015,A1 .Location in patent: Paragraph 0189; 0190

44
[ 35661-39-3 ]
[ 111524-95-9 ]
C₁₁H₁₄N₃O₂Pol [ No CAS ]

Reference： [1]ACS Combinatorial Science,2015,vol. 17,p. 152 - 155

45
[ 35661-38-2 ]
[ 111524-95-9 ]
C₁₁H₁₄N₃O₂Pol [ No CAS ]

Reference： [1]ACS Combinatorial Science,2015,vol. 17,p. 152 - 155

46
[ 111524-95-9 ]
[ 140-88-5 ]
(R,E)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(2-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)acetic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 9877 - 9884

47
[ 29022-11-5 ]
[ 92122-45-7 ]
[ 129460-09-9 ]
[ 111524-95-9 ]
Fmoc-Orn(Dde)-OH [ No CAS ]
H-Orn(Dde)-D-Lys(Boc)-D-Phg-isoAsp(OtBu)-Gly-OH [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 1540 - 1543
Angew. Chem.,2016,vol. 128,p. 1564 - 1568,5

48
[ 1724-17-0 ]
[ 111524-95-9 ]
methyl 3β-O-(N-fluorenonemethyoxycarbonyl)-phenylglycylurs-12-ene-28β-oate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.1%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 5.08h;	A solution of compound 3 (400 mg, 0.86 mmol) and <strong>[111524-95-9]Fmoc-D-phenylglycine</strong> (382 mg, 1.02 mmol) in dry methylene chloride (7 mL) was added to 4-dimethylaminopyridine (124 mg, 1.02 mmol) and stirred. A solution of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (197 mg, 1.02 mmol in dry dichloromethane (3 mL)) was added drop-wise to the reaction mixture at 0C and the mixture was stirred for 5 min at 0C, followed by additional stirring for 5 h at room temperature. The reaction mixture was then diluted with methylene chloride (50 mL) and washed with water (15 mL×3) and saturated sodium chloride solution (30 mL). The organic layer was dried over anhydrous magnesium sulfate. The residue was filtered, the remaining solvent was removed by evaporation at reduced pressure, and the isolated material was purified by silica gel chromatography with a gradient elution of ethyl acetate-petrol ether (1 : 10, v/v) and the obtained white solid was recrystallized from methanol, providing 3a (410 mg, 58.1%) as colorless solid; mp 117.7-118.6C; 1H-NMR (500 MHz, CDCl3) delta: 7.76 (d, 2H, J=7.5 Hz, fluorenyl H-4, H-5), 7.58 (d, 2H, J=6.2 Hz, fluorenyl H-1, H-8), 7.30-7.41 (m, 9H, fluorenyl H-2, H-7, H-6, H-3, 5×Ph-H), 5.99 (dd, J=6.8 Hz, 1H, CH-NH-CO), 5.32 (dd, 1H, J=7.1 Hz, CH-NH-CO), 5.25 (t, 1H, J=3.5 Hz, H-12), 4.47-4.58 (m, 1H, H-3), 4.39 (m, 2H, -CHCH2OCONH-), 4.25 (m, 1H, fluorenyl H-9), 3.60 (s, 3H, OCH3), 2.85 (dd, 1H, J=14 Hz, H-18), 1.08, 0.95, 0.93, 0.87, 0.75, 0.67, 0.48 (s, each 3H); 13C-NMR (125 MHz, CDCl3) delta: 178.28, 143.86, 128.85, 127.71, 127.21, 127.09, 119.99, 82.99, 55.26, 51.52, 47.21, 45.91, 41.68, 39.31, 38.07, 37.90, 37.77, 36.91, 33.90, 33.12, 32.59, 30.72, 27.71, 25.91, 23.66, 23.43, 23.10, 18.06, 16.85, 16.35, 15.30; IR numax(KBr, cm-1): 3340, 2922, 1730, 1577, 1472; ESI-MS: m/z825.82 [M-H]-. Anal.Calcd for C54H67NO6: C, 78.51; H, 8.17; N, 1.70. Found: C, 78.41; H, 8.03; N, 1.59

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 764 - 771

49
[ 1724-17-0 ]
[ 111524-95-9 ]
methyl 3β-O-phenylglycylurs-12-ene-28-oate [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 764 - 771

50
[ 915-32-2 ]
[ 111524-95-9 ]
methyl 3β-O-(N-fluorenonemethyoxycarbonyl)-phenylglycylurs-12-ene-28β-oate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.7%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 5.08h;	General procedure: A solution of compound 3 (400 mg, 0.86 mmol) and <strong>[111524-95-9]Fmoc-D-phenylglycine</strong> (382 mg, 1.02 mmol) in dry methylene chloride (7 mL) was added to 4-dimethylaminopyridine (124 mg, 1.02 mmol) and stirred. A solution of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (197 mg, 1.02 mmol in dry dichloromethane (3 mL)) was added drop-wise to the reaction mixture at 0C and the mixture was stirred for 5 min at 0C, followed by additional stirring for 5 h at room temperature. The reaction mixture was then diluted with methylene chloride (50 mL) and washed with water (15 mL×3) and saturated sodium chloride solution (30 mL). The organic layer was dried over anhydrous magnesium sulfate. The residue was filtered, the remaining solvent was removed by evaporation at reduced pressure, and the isolated material was purified by silica gel chromatography with a gradient elution of ethyl acetate-petrol ether (1 : 10, v/v) and the obtained white solid was recrystallized from methanol, providing 3a(410 mg, 58.1%) as colorless solid

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 764 - 771

51
[ 915-32-2 ]
[ 111524-95-9 ]
methyl 3β-O-phenylglycylurs-12-ene-28β-oate [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 764 - 771

52
[ 1477-44-7 ]
[ 111524-95-9 ]
methyl 3β-O-(N-fluorenylmethoxycarbonyl)-phenylglycyl-11-oxo-olean-12-en-30-oate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.9%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 3h;	A solution of compound 1(500 mg, 1.03 mmol), <strong>[111524-95-9]Fmoc-D-phenylglycine</strong> (578.7 mg, 1.55 mmol), and N,N-dimethylaminopyridine (DMAP) (189.3 mg, 1.55 mmol) in methylene chloride (5 mL) was added to 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (197.1 mg, 1.55 mmol) at 0C and stirred for 3 h at room temperature. The reaction mixture was then diluted with methylene chloride and washed with water and saturated sodium chloride solution (10 mL). The solution was filtered, the remaining solvent was removed by evaporation at reduced pressure, and the isolated material was purified by silica gel chromatography using a gradient elution of ethyl acetate-petroleum ether (1 : 5, v/v) to afford a white solid (347.2 mg, 40.9%), mp 125.4-126.0C; 1H-NMR (500 MHz, CDCl3) delta: 7.68 (d, J=7.4 Hz, 2H, fluorenyl H-4?, H-5?), 7.51 (d, J=4.0 Hz, 2H, fluorenyl H-1?, H-8?), 7.32 (d, J=7.0 Hz, 2H, fluorenyl H-3?, H-6?), 7.23 (d, J=6.5 Hz, 2H, fluorenyl H-2?, H-7?), 7.34 -7.21, (m, 5H, Ph-H), 5.96 (d, J=7.1 Hz, 1H, Ph-CH), 5.58 (s, 1H, H-12), 5.88 (d, J=6.9 Hz, 1H, -NH-), 5.20-5.16 (m, 1H, H-2), 4.52-4.42 (m, 2H, -CH2O-), 4.19 (t, J=7.0 Hz, 1H, fluorenyl H-9?), 3.53 (s, 3H, -OCH3), 2.72 (dt, J1=14.0 Hz, J2=3.9 Hz, 1H, H-18), 2.25 (s, 1H, H-9), 1.07, 0.89, 0.85, 0.80,0.79 (s, each 3H, -CH3), 0.71 (s, 6H, -CH3×2); 13C-NMR (125 MHz, CDCl3) delta: 199.92, 176.93, 169.26, 143.91, 128.89, 128.84, 128.54, 128.51, 125.12, 82.70, 77.29, 77.03, 76.78, 67.15, 61.67, 55.05, 51.78, 48.45, 47.21, 45.40, 44.08, 43.24, 41.15, 38.73, 38.25, 38.11, 37.78, 36.92, 32.69, 31.87, 31.18, 29.72, 28.54, 28.34, 26.46, 23.70, 23.37, 22.68, 19.20, 18.70, 17.38, 17.24, 16.65, 16.35, 14.42, 14.12; IR numax(KBr, cm-1): 3439, 2954, 2890, 1710, 1532, 1438, 1369, 1206, 1156, 796, 710; ESI-MS: m/z839.83 [M-H]-. Anal.Calcd for C54H65NO7: C, 77.20; H, 7.80; N, 1.67. Found: C, 77.13; H, 7.75; N, 1.66.

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 764 - 771

53
[ 1477-44-7 ]
[ 111524-95-9 ]
methyl 3β-O-phenylglycyl-11-oxo-olean-12-en-30-oate [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 764 - 771

54
[ 86123-10-6 ]
[ 111524-95-9 ]
[ 57-11-4 ]
C₃₅H₅₂N₂O₄ [ No CAS ]

Reference： [1]Langmuir,2016,vol. 32,p. 7420 - 7426

55
[ 86123-10-6 ]
[ 111524-95-9 ]
[ 57-11-4 ]
C₃₅H₅₂N₂O₄ [ No CAS ]

Reference： [1]Langmuir,2016,vol. 32,p. 7420 - 7426

56
[ 35661-40-6 ]
[ 111524-95-9 ]
[ 57-11-4 ]
C₃₅H₅₂N₂O₄ [ No CAS ]

Reference： [1]Langmuir,2016,vol. 32,p. 7420 - 7426

57
[ 35661-40-6 ]
[ 111524-95-9 ]
[ 57-11-4 ]
C₃₅H₅₂N₂O₄ [ No CAS ]

Reference： [1]Langmuir,2016,vol. 32,p. 7420 - 7426

58
[ 35661-40-6 ]
[ 111524-95-9 ]
[ 65-85-0 ]
Bz-(L)-Phe-(D)-Phg-NH₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2325 - 2329

59
[ 875-74-1 ]
[ 82911-69-1 ]
[ 111524-95-9 ]