[ CAS No. 103478-58-6 ] {[proInfo.proName]}

Name: 103478-58-6|Fmoc-D-N-Me-Val-OH|97%
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SKU: A219181
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Quality Control of [ 103478-58-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 103478-58-6 ]

SDS Specification

Alternatived Products of [ 103478-58-6 ]

Product Details of [ 103478-58-6 ]

CAS No. :	103478-58-6	MDL No. :	MFCD00153396
Formula :	C₂₁H₂₃NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YCXXXPZNQXXRIG-LJQANCHMSA-N
M.W :	353.41	Pubchem ID :	16213159
Synonyms :

Calculated chemistry of [ 103478-58-6 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.33
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	99.69
TPSA :	66.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.62
Log Po/w (XLOGP3) :	4.2
Log Po/w (WLOGP) :	3.98
Log Po/w (MLOGP) :	3.0
Log Po/w (SILICOS-IT) :	3.11
Consensus Log Po/w :	3.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-4.56
Solubility :	0.00981 mg/ml ; 0.0000278 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.31
Solubility :	0.00172 mg/ml ; 0.00000486 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.98
Solubility :	0.00373 mg/ml ; 0.0000105 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.63

Safety of [ 103478-58-6 ]

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 [ 103478-58-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 103478-58-6 ]
Downstream synthetic route of [ 103478-58-6 ]

[ 103478-58-6 ] Synthesis Path-Upstream 1~6

1
[ 84000-01-1 ]
[ 103478-58-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylsilane; trifluoroacetic acid In chloroform at 20℃;	The Fmoc-valinyloxazolidinone (2.80g, 8.00mmol) was dissolved in chloroform (40mL). To this solution, trifluoroacetic acid (1.85mL, 24.0equiv) and triethylsilane (3.83mL, 24.0equiv) were added. The mixture was stirred at room temperature and left until the reaction was complete (24–72h). The solution was concentrated and partitioned between ether and 5percent sodium bicarbonate solution. The combined aqueous phases were acidified with 5M hydrochloric acid until reaching pH 2 and then it was extracted with ethyl acetate. The desired organic phase was dried (MgSO₄) and concentrated to give Fmoc-N-methylvaline 4 as a white solid (2.35g, 83percent). Recrystallisation of Fmoc-N-methylvaline using ethyl acetate gave white needles: mp 186–187°C (lit.³³ mp 185–187°C); LRMS (ESI) m/z [M+H]⁺ 354.1 (100percent) [M+Na]⁺ 376.1 (61percent); IR (NaCl) ν_max (cm⁻¹) 3420 (broad) (OH), 2964 (aliphatic CH), 1700 (C=O), 1445, 1305 (C=C); ¹H NMR (300MHz, CDCl₃) δ_H (ppm) 7.63 (2H, d, J=7.5Hz, ArH), 7.46 (2H, d, J=6.9Hz, ArH), 7.26 (2H, t, J=7.2Hz, ArH), 7.17 (2H, t, J=7.5Hz, ArH), 4.28 (2H, m, CHCH₂O), 4.22 (1H, m, (Ar)₂CHCH₂), 4.13 (1H, m, NCHCO), 2.79 (3H, d, J=4.2Hz, NCH₃), 2.02 (1H, m, CH₃CHCH₃), 0.88 (3H, dd, J=6.6, 19.2Hz, CH₃CHCH₃), 0.72 (3H, dd, J=6.6, 13.8Hz, CH₃CHCH₃) (IR and ¹H NMR data were in agreement with that previously described);³³ ¹³C NMR (75MHz, CDCl₃) δ_C (ppm) 175.5, 159.6, 146.6, 143.9, 130.4, 129.7, 127.7, 122.6, 70.3, 66.9, 49.9, 33.1, 30.2, 22.5, 21.7.

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6918 - 6920
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2351 - 2358

2
[ 1220527-59-2 ]
[ 103478-58-6 ]

Reference： [1] Amino Acids, 2010, vol. 38, # 1, p. 133 - 143

3
[ 1208119-51-0 ]
[ 28920-43-6 ]
[ 103478-58-6 ]

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 5, p. 1386 - 1392

4
[ 68858-20-8 ]
[ 103478-58-6 ]

Reference： [1] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[2] Tetrahedron, 2014, vol. 70, # 14, p. 2351 - 2358

5
[ 186581-53-3 ]
[ 28920-43-6 ]
[ 270073-00-2 ]
[ 103478-58-6 ]

Reference： [1] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3723 - 3728

6
[ 67-56-1 ]
[ 72-18-4 ]
[ 28920-43-6 ]
[ 103478-58-6 ]

Reference： [1] Tetrahedron Letters, 1997, vol. 38, # 42, p. 7307 - 7310

[ 103478-58-6 ] Synthesis Path-Downstream 1~88

1
[ 3339-44-4 ]
[ 103478-58-6 ]
[ 142350-38-7 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 2815 - 2816
[2]Journal of Organic Chemistry,1994,vol. 59,p. 2437 - 2446

2
[ 6306-52-1 ]
[ 103478-58-6 ]
<N-<<(9-Fluorenylmethyl)oxy>carbonyl>-N-methyl-L-valyl>-L-valine methyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2437 - 2446

3
[ 81135-38-8 ]
[ 103478-58-6 ]
(S)-2-({(S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-methyl-butyryl}-methyl-amino)-3-methyl-butyric acid benzyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 4342 - 4343

4
[ 103478-58-6 ]
Bis-(S)-<N-<<(9-fluorenylmethyl)oxy>carbonyl>-N-methyl-2-amino-3-methylbutanoic> anhydride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2437 - 2446

5
[ 103478-58-6 ]
[ 103478-72-4 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[2]Journal of Organic Chemistry,2007,vol. 72,p. 9360 - 9363
[3]Journal of Organic Chemistry,2011,vol. 76,p. 6686 - 6693

6
[ 67-56-1 ]
[ 72-18-4 ]
[ 28920-43-6 ]
[ 103478-58-6 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 7307 - 7310

7
[ 103478-58-6 ]
[ 205498-80-2 ]
[ 205498-84-6 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1524 - 1530

8
[ 103478-62-2 ]
[ 35661-38-2 ]
[ 103478-58-6 ]
Abu-Sar-MeLeu-Val-MeLeu-Ala-PAC-polystyrene resin [ No CAS ]
Fmoc-D-Ala-MeLeu-MeLeu-MeVal-MeLeu-Abu-Sar-MeLeu-Val-MeLeu-Ala-OH [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 7279 - 7280

9
[ 71989-28-1 ]
[ 108-91-8 ]
[ 79-08-3 ]
[ 103478-58-6 ]
Boc-Cys(Trt) [ No CAS ]
(S)-2-[2-({(S)-2-[((R)-2-Amino-3-mercapto-propionyl)-methyl-amino]-3-methyl-butyryl}-cyclohexyl-amino)-acetylamino]-4-methylsulfanyl-butyric acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 85 - 92

10
[ 71989-28-1 ]
[ 108-91-8 ]
[ 79-08-3 ]
[ 103478-58-6 ]
Boc-Cys(Trt) [ No CAS ]
(S)-2-[2-({(S)-2-[((R)-2-tert-Butoxycarbonylamino-3-mercapto-propionyl)-methyl-amino]-3-methyl-butyryl}-cyclohexyl-amino)-acetylamino]-4-methylsulfanyl-butyric acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 85 - 92

11
[ 40298-32-6 ]
[ 103478-58-6 ]
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-valyl-sarcosine benzyl ester [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 4437 - 4445

12
[ 103478-58-6 ]
5-(1H-benzotriazol-1-yloxy)-3,4-dihydro-1-methyl-2H-pyrrolium hexachloroantimonate [ No CAS ]
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methylvaline benzotriazolyl ester [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 4437 - 4445

13
[ 103478-62-2 ]
[ 35661-38-2 ]
[ 103478-58-6 ]
[ 115141-96-3 ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 8119 - 8131
[2]Journal of Organic Chemistry,2000,vol. 65,p. 2951 - 2958

14
[ 103478-58-6 ]
benzyl 2-(methylamino)acetate trifluoroacetic acid salt [ No CAS ]
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-valyl-sarcosine benzyl ester [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 9949 - 9955

15
[ 40298-32-6 ]
[ 103478-58-6 ]
5-(1H-benzotriazol-1-yl)-3,4-dihydro-1-methyl-2H-pyrrolium hexachloroantimonate N-oxide [ No CAS ]
methyl-[2-methyl-1-(3-oxy-benzotriazole-1-carbonyl)-propyl]-carbamic acid 9<i>H</i>-fluoren-9-ylmethyl ester [ No CAS ]
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methylvaline benzotriazolyl ester [ No CAS ]
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-valyl-sarcosine benzyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 113 - 120

16
[ 68858-20-8 ]
[ 35737-15-6 ]
[ 103478-58-6 ]
[ 77128-70-2 ]
Fmoc-MeIle-OHFmoc-Ile-OH [ No CAS ]
cyclo(Trp-MeVal-Ile-MeVal-MeVal-Sar-MeVal-MeIle-Sar-Val-MeIle-Sar) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition in English,2002,vol. 41,p. 2307 - 2309

17
[ 104-03-0 ]
[ 118-31-0 ]
[ 103478-58-6 ]
[ 18637-83-7 ]
2-[4-(3-isopropyl-4-methyl-2,5,6-trioxo-piperazin-1-yl)-phenyl]-<i>N</i>-naphthalen-1-ylmethyl-acetamide [ No CAS ]

Reference： [1]Synlett,2003,p. 817 - 820

18
[ 68858-20-8 ]
[ 35661-39-3 ]
[ 103478-62-2 ]
[ 103478-58-6 ]
Fmoc-Nva-OHFMoc-D-Ala-OH [ No CAS ]
cyclosporin O [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 5013 - 5016

19
[ 1111-97-3 ]
[ 103478-58-6 ]
N-(9-fluorenylmethoxycarbonyl)-N-methyl-valine dimethylpropargyl ester [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1473 - 1475

20
[ 84000-01-1 ]
[ 103478-58-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylsilane; trifluoroacetic acid; In chloroform; at 20℃;	The Fmoc-valinyloxazolidinone (2.80g, 8.00mmol) was dissolved in chloroform (40mL). To this solution, trifluoroacetic acid (1.85mL, 24.0equiv) and triethylsilane (3.83mL, 24.0equiv) were added. The mixture was stirred at room temperature and left until the reaction was complete (24-72h). The solution was concentrated and partitioned between ether and 5% sodium bicarbonate solution. The combined aqueous phases were acidified with 5M hydrochloric acid until reaching pH 2 and then it was extracted with ethyl acetate. The desired organic phase was dried (MgSO4) and concentrated to give Fmoc-N-methylvaline 4 as a white solid (2.35g, 83%). Recrystallisation of Fmoc-N-methylvaline using ethyl acetate gave white needles: mp 186-187C (lit.33 mp 185-187C); LRMS (ESI) m/z [M+H]+ 354.1 (100%) [M+Na]+ 376.1 (61%); IR (NaCl) numax (cm-1) 3420 (broad) (OH), 2964 (aliphatic CH), 1700 (C=O), 1445, 1305 (C=C); 1H NMR (300MHz, CDCl3) deltaH (ppm) 7.63 (2H, d, J=7.5Hz, ArH), 7.46 (2H, d, J=6.9Hz, ArH), 7.26 (2H, t, J=7.2Hz, ArH), 7.17 (2H, t, J=7.5Hz, ArH), 4.28 (2H, m, CHCH2O), 4.22 (1H, m, (Ar)2CHCH2), 4.13 (1H, m, NCHCO), 2.79 (3H, d, J=4.2Hz, NCH3), 2.02 (1H, m, CH3CHCH3), 0.88 (3H, dd, J=6.6, 19.2Hz, CH3CHCH3), 0.72 (3H, dd, J=6.6, 13.8Hz, CH3CHCH3) (IR and 1H NMR data were in agreement with that previously described);33 13C NMR (75MHz, CDCl3) deltaC (ppm) 175.5, 159.6, 146.6, 143.9, 130.4, 129.7, 127.7, 122.6, 70.3, 66.9, 49.9, 33.1, 30.2, 22.5, 21.7.

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 6918 - 6920
[2]European Journal of Organic Chemistry,2013,p. 4509 - 4513
[3]Tetrahedron,2014,vol. 70,p. 2351 - 2358

21
Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate [ No CAS ]
[ 103478-58-6 ]
N-(9-fluorenylmethoxycarbonyl)-N-methyl-valine 1,1-dimethylallyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 9517 - 9518

22
L-MeCys(Acm)-OMe [ No CAS ]
[ 103478-58-6 ]
(R)-3-(Acetylamino-methylsulfanyl)-2-({(S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-methyl-butyryl}-methyl-amino)-propionic acid methyl ester [ No CAS ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

23
[ 851706-65-5 ]
[ 103478-58-6 ]
[ 851706-66-6 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

24
[ 864814-68-6 ]
[ 103478-58-6 ]
[ 864814-69-7 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

25
[ 851706-59-7 ]
[ 103478-58-6 ]
[ 851706-60-0 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

26
[ 851706-40-6 ]
[ 103478-58-6 ]
[ 851706-46-2 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

27
[ 186581-53-3 ]
[ 28920-43-6 ]
[ 270073-00-2 ]
[ 103478-58-6 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3723 - 3728

28
[ 84000-07-7 ]
[ 103478-58-6 ]
[ 84000-14-6 ]
all-N-Me-(Ser(OBz)-Val-Ala-Ser(OBz)-Val-Ala) [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 497 - 499

29
[ 103478-58-6 ]
L-MeVal-ox-[L-MeCys-D-MeCys]-L-Pha-OH [ No CAS ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

30
[ 103478-58-6 ]
L-MeVal-ox-[L-MeCys-L-MeCys]-L-Pha-OH [ No CAS ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

31
[ 103478-58-6 ]
[ 851706-56-4 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

32
[ 103478-58-6 ]
[ 851706-50-8 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

33
[ 103478-58-6 ]
[ 851706-55-3 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

34
[ 103478-58-6 ]
[ 851706-48-4 ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

35
[ 103478-58-6 ]
N-Fmoc-L-MeVal-ox-[L-MeCys-L-MeCys]-L-Pha-OAc [ No CAS ]

Reference： [1]Heterocycles,2005,vol. 65,p. 563 - 578

36
[ 103478-58-6 ]
N-(9-fluorenylmethoxycarbonyl)-N-methyl-valine 1,1-dimethylallyl ester [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1473 - 1475

37
[ 103478-58-6 ]
(2R,3R)-3-Methoxy-2-methyl-3-{(S)-1-[(S)-1-((S)-3-methyl-2-methylamino-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidin-2-yl}-N-((S)-2-phenyl-1-thiazol-2-yl-ethyl)-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1524 - 1530

38
[ 103478-58-6 ]
(S)-2-Amino-N-[(S)-1-((S)-2-{(S)-2-[(1R,2R)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-3,N-dimethyl-butyramide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1524 - 1530

39
[ 103478-58-6 ]
(S)-2-Dimethylamino-N-((S)-1-[(S)-1-((S)-2-{(S)-2-[(1R,2R)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-methyl-carbamoyl}-2-methyl-propyl)-3-methyl-butyramide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1524 - 1530

40
[ 103478-58-6 ]
[ 205498-86-8 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1524 - 1530

41
[ 103478-58-6 ]
[ 5616-87-5 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

42
[ 103478-58-6 ]
[ 103478-69-9 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[2]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[3]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[4]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

43
[ 103478-58-6 ]
[ 89537-03-1 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[2]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

44
[ 103478-58-6 ]
[ 89537-02-0 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

45
[ 103478-58-6 ]
[ 89537-04-2 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[2]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

46
[ 103478-58-6 ]
[ 103478-71-3 ]

47
[ 103478-58-6 ]
Fmoc-Ala-MeLeu-MeLeu-MeVal-O-t-Bu [ No CAS ]

48
[ 103478-58-6 ]
[ 103478-59-7 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

49
[ 103478-58-6 ]
[ 103478-64-4 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

50
[ 103478-58-6 ]
(S)-2-({(R)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-4-methyl-pentanoyl}-methyl-amino)-3-methyl-butyric acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

51
[ 103478-58-6 ]
[ 103478-67-7 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[2]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

52
[ 103478-58-6 ]
Fmoc-D-MeLeu-MeLeu-MeVal-O-t-Bu [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354
[2]Journal of Organic Chemistry,1986,vol. 51,p. 3350 - 3354

53
[ 68641-49-6 ]
[ 103478-58-6 ]
(R*)-N-[[2-[N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl]-1,2,3,4-tetrahydro-3-isoquinolinyl]carbonyl]-L-methionine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	A.(R*)-N-[[2-[N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl]-1,2,3,4-tetrahydro-3-isoquinolinyl]carbonyl]-L-methionine, methyl ester. Compound 1A (2.0 g, 4.733 mmol), was N-deprotected using the procedure described in the preparation of Compound 7A. The resulting amine hydrochloride was dissolved in CH2Cl2 (20 mL) and cooled to 0C. Fmoc-N-methyl-L-valine (1.67 g, 4.733 mmol), bis-(2-oxo-3-oxazolidinyl)phosphinic chloride (2.41 g, 9.467 mmol) and N,N-diisopropylethylamine (2.45 g, 3.3 mL, 18.9 mmol) were added. The reaction mixture was stirred for 4 hours at 0C. The reaction mixture was concentrated and chromatographed (silica gel, eluding with 40% ethyl acetate, 60% hexane) to yield Compound A as a white glass (2.4g, 78%).

Reference： [1]Patent: EP618221,1994,A2

54
[ 74124-79-1 ]
[ 103478-58-6 ]
[ 863971-49-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 3h;	[0616] To a room temperature suspension of Fmoc-MeVal-OH (3.03 g, 8.57 mmol) and N,N'-disuccimidyl carbonate (3.29 g, 12.86 mmol) in CH2Cl2 (80 mL) is added DIEA (4.48 mL, 25.71 mmol). This reaction mixture is allowed to stir for 3 hr, and then poured into a separation funnel where the organic mixture is extracted with 0.1 M HCl (aq). The crude organic residue is concentrated under reduced pressure, and the product is isolated by flash column chromatography on silica gel using a 20-100% ethyl acetate/hexanes linear gradient {e.g., a total of 2.18 g of pure Fmoc-MeVal-OSu (4.80 mmoles, 56% yield) can be recovered).
56%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 3h;	[0561] To a room temperature suspension of Fmoc-MeVal-OH (3.03 g, 8.57 mmol) andN,N'-disuccimidyl carbonate (3.29 g, 12.86 mmol) in CH2Cl2 (80 mL) is added DIEA (4.48 mL, 25.71 mmol). This reaction mixture is allowed to stir for 3 hr, and then poured into a separation funnel where the organic mixture is extracted with 0.1 M HCl (aq). The crude organic residue is concentrated under reduced pressure, and the product is isolated by flash column chromatography on silica gel using a 20-100% ethyl acetate/hexanes linear gradient. A total of 2.18 g of pure Fmoc-MeVal-OSu (4.80 mmoles, 56% yield) is EPO <DP n="172"/>recovered. To a room temperature suspension of Fmoc-MeVal-OSu (2.18 g, 4.84 mmol) in DME (13 niL) and THF (6.5 mL) is added a solution of L-citrulline (0.85 g, 4.84 mmol) and NaHCO3 (0.41 g, 4.84 mmol) in H2O (13 mL). The suspension is allowed to stir at room temperature for 16 hr, then it is extracted into ter?-BuOH/CHCl3/H2O, acidified to pH=2-3 with 1 M HCl. The organic phase is separated, dried and concentrated under reduced pressure. The residue is triturated with diethyl ether resulting in 2.01 g of Fmoc-MeVal-Cit-COOH which is used without further purification.
56%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h;	To a room temperature suspension of Fmoc-MeVal-OH (3.03 g, 8.57 mmol) and N,N?-disuccimidyl carbonate(3.29 g, 12.86 mmol) in CH2Cl2 (80 mL) was added DIEA (4.48 mL, 25.71 mmol). This reaction mixture was allowed tostir for 3.0 hr, and then poured into a separation funnel where the organic mixture was extracted with 0.1 M HCl (aq).The crude organic residue was concentrated under reduced pressure, and the product was isolated by flash columnchromatography on silica gel using a 20-100% ethyl acetate/hexanes linear gradient. A total of 2.18 g of pure Fmoc-MeVal-OSu (4.80 mmoles, 56% yield) was recovered.

Reference： [1]Patent: WO2007/8603,2007,A1 .Location in patent: Page/Page column 227
[2]Patent: WO2007/8848,2007,A2 .Location in patent: Page/Page column 170; 171
[3]Patent: EP2486933,2015,B1 .Location in patent: Paragraph 0568

Yield	Reaction Conditions	Operation in experiment
	Reactivity (does not react);	EXAMPLES Comparative Solid-Phase Peptide Syntheses; The reactivity of PyClock as a coupling agent in solid-phase peptide syntheses was tested and compared with that of PyBOP. To this end, solid phase syntheses of various peptides, which are considered difficult to prepare by conventional synthetic approaches, were performed.Materials and Experimental Methods:6-chloro- 1 -hydroxybenzotriazol- 1 -yl-N-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyClock) was prepared as described in Example 1. The following Fmoc-N-protected amino acids were used: tyrosine (Fmoc-L-Tyr(tBu)-OH), N-methylvaline (Fmoc-L-NMeVal-OH), aminoisobutyric acid (Fmoc-Aib-OH), phenylalanine (Fmoc-L-Phe-OH), leucine (Fmoc-L-Leu-OH) and arginine (Fmoc-L-Arg(Pbf)-OH).Peptide Syntheses: Solid phase peptide syntheses were carried out in polypropylene syringes (10 ml) fitted with a polyethylene porous disc, using general Fmoc chemistry, as follows:AU procedures were performed at 25 C. Each cycle included Fmoc deprotection, washing, coupling an amino acid to the resin-bound peptidyl in the presence of the tested coupling agent and washing. Fmoc deprotection was carried out using 20 % piperidine in DMF (1 x 1 minute, 2 x 10 minutes).Washings between repetitive cycles of deprotection and coupling were carried out using DMF (5 x 1 minutes, 10 ml solvent per 1 gram of resin). EPO <DP n="40"/>5 molar equivalents of a Fmoc-protected amino acid, 5 molar equivalents of the tested coupling agent and 15 molar equivalents of N,N-diisopropylethylamine (DIEA) were reacted with 1 molar equivalent of a resin in each cycle.Thus, DMF (0.2 ml) was added to a mixture of a first Fmoc-protected amino acid, a coupling agent and DIEA and after 5 minutes the resulting mixture was added to the Rink resin (50 mg, 0.66 mmol/gram). Upon washing, Fmoc deprotection and washing, a mixture containing a second Fmoc protected amino acid and a coupling agent was reacted with the resin, as described above. This procedure was repeated until the peptide synthesis was completed.Upon completion, the peptide was cleaved from the resin by treatment with neat TFA for 1 hour, to remove residual Fmoc and other protection groups. MethyW- butylether was then added to the resulting peptide and the resulting solid precipitate was isolated by means of centrifugation. Precipitation was performed trice and the isolated peptide was then subjected to lyophilization.Table 5 below presents the results of the comparative solid-phase peptide synthesis using PyClock, the peptide coupling agent of the present invention, and PyBOP, by reporting the overall yield of synthesis for each peptide coupling agent.

56
Fmoc-gly-wang resin [ No CAS ]
[ 71989-14-5 ]
[ 103478-58-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
Fmoc-p-amino(Boc)-D-Phe-OH [ No CAS ]
C₄₉H₇₄N₉O₁₃PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%		Synthesis of bicyclic-RGD-4C-tether 4. Acyclic RGD-4C-tether 3 (30 mg) was dissolved in a solution of 50 mL of TFA and 2.5 mL of dimethyl sulfoxide. Anisole (0.5 mL) was then added by syringe with stirring and the solution stirred for 1 h. The reaction was monitored by HPLC and stopped when complete (usually 1 h). The solution was then concentrated under high vacuum to yield a mixture (approximately 50: 50) of bicyclic isomers. HPLC gave two peaks at r. t. , 27.05 and 27.31 min for the two isomers; ESI-MS, m/z 1175.6, calculated for (M+H+) 1175.4 for both isomers, Synthesis of protected acyclic-N-Me-VRGDf-NH2, 5: General Fmoc synthesis was performed as for acyclic-RGD-4C-tether, but TBTU/HOBt coupling was found to be inefficient for coupling to N-methyl valine. Peptide still on the resin was treated with 2 equiv. PyBroP, Fmoc-D-4-aminophe (Boc) and 4 equiv. DIEA in dry dichloromethane (5 mL per gram resin). The mixture was placed on a shaker for 16 h, washed with 3 x 10 mL of dichloromethane, and checked by the chloranil test for coupling completion. If not complete, coupling was repeated for 3 h. When coupling was finished, the resin was then treated with 3 x 10 mL of 20% piperidine in DMF for a period of 10 min to complete deprotection. Resin was then returned to the ABI synthesizer to complete the peptide synthesis using standard Fmoc synthesis protocol. Cleavage of the linear peptide was effected with 1% TFA in dichloromethane (3 x 10 mL) with shaking for 5 min each time. The solution was concentrated under high vacuum to give the linear peptide with protecting groups intact in 98% yield as determined by analytical HPLC (one peak with r. t. , 17.9 min);

Reference： [1]Patent: WO2005/34856,2005,A2 .Location in patent: Page/Page column 114

57
[ 103478-58-6 ]
[ 172372-42-8 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14382 - 14383

58
C₃₇H₄₆ClN₄O₆Pol [ No CAS ]
[ 103478-58-6 ]
C₅₈H₆₇ClN₅O₉Pol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3194 - 3202

59
[ 1208119-51-0 ]
[ 28920-43-6 ]
[ 103478-58-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1386 - 1392

60
[ 29022-11-5 ]
[ 103478-62-2 ]
[ 108-24-7 ]
[ 71989-28-1 ]
[ 103478-58-6 ]
[ 138775-22-1 ]
[ 960324-14-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 8002 - 8009

61
[ 103478-62-2 ]
[ 108-24-7 ]
[ 71989-28-1 ]
[ 103478-58-6 ]
[ 77128-70-2 ]
[ 138775-22-1 ]
[ 960324-16-7 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 8002 - 8009

62
[ 847663-65-4 ]
C₂₅H₃₂N₄O₄ [ No CAS ]
[ 29022-11-5 ]
[ 71989-14-5 ]
[ 103478-58-6 ]
[ 76-05-1 ]
C₂HF₃O₂*C₂₇H₃₉N₇O₈ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 2732 - 2737

63
[ 1308252-44-9 ]
[ 29022-11-5 ]
[ 71989-14-5 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
[ 76-05-1 ]
C₂HF₃O₂*C₂₇H₃₉N₇O₈ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 2732 - 2737

64
[ 7788-77-4 ]
C₂₅H₃₂N₄O₄ [ No CAS ]
[ 71989-14-5 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
[ 76-05-1 ]
C₂HF₃O₂*C₂₇H₃₉N₇O₈ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 2732 - 2737

65
C₂₅H₃₂N₄O₄ [ No CAS ]
[ 29022-11-5 ]
[ 71989-14-5 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
[ 76-05-1 ]
cilengitide trifluoroacetate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 2732 - 2737

66
C₂₅H₃₂N₄O₄ [ No CAS ]
[ 29022-11-5 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
[ 76-05-1 ]
allyl [(5S)-2,2-bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl]acetate [ No CAS ]
C₂HF₃O₂*C₂₇H₃₉N₇O₈ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 2732 - 2737

67
[ 1220527-59-2 ]
[ 103478-58-6 ]

Reference： [1]Amino Acids,2010,vol. 38,p. 133 - 143

68
Fmoc-Leu-preloaded Wang resin, deprotected [ No CAS ]
Fmoc-β-OH-Phe-OH [ No CAS ]
[ 35661-60-0 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
C₃₆H₅₃N₅O₇ [ No CAS ]
C₃₆H₅₃N₅O₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6822 - 6856

69
Fmoc-Leu-preloaded Wang resin, deprotected [ No CAS ]
(+/-)-Fmoc-threo-β-phenylserine [ No CAS ]
[ 35661-60-0 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
C₃₆H₅₃N₅O₇ [ No CAS ]
C₃₆H₅₃N₅O₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6822 - 6856

70
Fmoc-Leu-preloaded Wang resin, deprotected [ No CAS ]
[ 86060-82-4 ]
[ 35661-40-6 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
NH₂-Phe-D-Phe-Lys(Z)-N-Me-Val-Leu-OH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6822 - 6856

71
Fmoc-Leu-preloaded Wang resin, deprotected [ No CAS ]
[ 35661-40-6 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
Fmoc-Lys(ClZ)-OH [ No CAS ]
NH₂-Phe-D-Phe-Lys(2-Cl-Z)-N-Me-Val-Leu-OH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6822 - 6856

72
C₂₆H₂₇N₂O₃Pol [ No CAS ]
[ 103478-58-6 ]
C₄₇H₄₈N₃O₆Pol [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3792 - 3795

73
C₃₉H₄₅N₄O₆Pol [ No CAS ]
[ 103478-58-6 ]
C₆₀H₆₆N₅O₉Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLES Comparative Solid-Phase Peptide Syntheses; The reactivity of PyClock as a coupling agent in solid-phase peptide syntheses was tested and compared with that of PyBOP. To this end, solid phase syntheses of various peptides, which are considered difficult to prepare by conventional synthetic approaches, were performed.Materials and Experimental Methods:6-chloro- 1 -hydroxybenzotriazol- 1 -yl-N-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyClock) was prepared as described in Example 1. The following Fmoc-N-protected amino acids were used: tyrosine (Fmoc-L-Tyr(tBu)-OH), N-methylvaline (Fmoc-L-NMeVal-OH), aminoisobutyric acid (Fmoc-Aib-OH), phenylalanine (Fmoc-L-Phe-OH), leucine (Fmoc-L-Leu-OH) and arginine (Fmoc-L-Arg(Pbf)-OH).Peptide Syntheses: Solid phase peptide syntheses were carried out in polypropylene syringes (10 ml) fitted with a polyethylene porous disc, using general Fmoc chemistry, as follows:AU procedures were performed at 25 C. Each cycle included Fmoc deprotection, washing, coupling an amino acid to the resin-bound peptidyl in the presence of the tested coupling agent and washing. Fmoc deprotection was carried out using 20 % piperidine in DMF (1 x 1 minute, 2 x 10 minutes).Washings between repetitive cycles of deprotection and coupling were carried out using DMF (5 x 1 minutes, 10 ml solvent per 1 gram of resin). EPO <DP n="40"/>5 molar equivalents of a Fmoc-protected amino acid, 5 molar equivalents of the tested coupling agent and 15 molar equivalents of N,N-diisopropylethylamine (DIEA) were reacted with 1 molar equivalent of a resin in each cycle.Thus, DMF (0.2 ml) was added to a mixture of a first Fmoc-protected amino acid, a coupling agent and DIEA and after 5 minutes the resulting mixture was added to the Rink resin (50 mg, 0.66 mmol/gram). Upon washing, Fmoc deprotection and washing, a mixture containing a second Fmoc protected amino acid and a coupling agent was reacted with the resin, as described above. This procedure was repeated until the peptide synthesis was completed.Upon completion, the peptide was cleaved from the resin by treatment with neat TFA for 1 hour, to remove residual Fmoc and other protection groups. MethyW- butylether was then added to the resulting peptide and the resulting solid precipitate was isolated by means of centrifugation. Precipitation was performed trice and the isolated peptide was then subjected to lyophilization.Table 5 below presents the results of the comparative solid-phase peptide synthesis using PyClock, the peptide coupling agent of the present invention, and PyBOP, by reporting the overall yield of synthesis for each peptide coupling agent.

Reference： [1]Patent: WO2007/20620,2007,A1 .Location in patent: Page/Page column 38-39

74
[ 84000-07-7 ]
[ 103478-58-6 ]
[ 77128-70-2 ]
[ 1219925-98-0 ]

Reference： [1]Journal of Peptide Science,2010,vol. 16,p. 136 - 140

75
[ 103478-58-6 ]
[ 77128-70-2 ]
[ 138775-22-1 ]
[ 1219925-96-8 ]

Reference： [1]Journal of Peptide Science,2010,vol. 16,p. 136 - 140

76
C₁₅H₂₂N₃O₂Pol [ No CAS ]
[ 112883-29-1 ]
[ 103478-58-6 ]
[ 926016-58-2 ]
C₂₁H₃₄N₄O₃ [ No CAS ]
C₂₇H₄₅N₅O₄ [ No CAS ]
[ 1301720-98-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4506 - 4513
[2]Journal of Organic Chemistry,2011,vol. 76,p. 4506 - 4513

77
C₁₅H₂₂N₃O₂Pol [ No CAS ]
[ 112883-29-1 ]
[ 103478-58-6 ]
C₂₁H₃₄N₄O₃ [ No CAS ]
C₂₇H₄₅N₅O₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4506 - 4513

78
C₁₅H₂₂N₃O₂Pol [ No CAS ]
[ 112883-29-1 ]
[ 103478-58-6 ]
[ 926016-58-2 ]
C₂₁H₃₄N₄O₃ [ No CAS ]
C₂₇H₄₅N₅O₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4506 - 4513

79
[ 2592-95-2 ]
[ 103478-58-6 ]
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methylvaline benzotriazolyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 6686 - 6693

80
[ 67-56-1 ]
[ 29022-11-5 ]
[ 71989-14-5 ]
[ 86123-10-6 ]
[ 103478-58-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₄₅H₆₈N₈O₁₁S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 9496 - 9500

81
Fmoc-Leu-preloaded Wang resin, deprotected [ No CAS ]
[ 103478-58-6 ]
C₂₇H₃₃N₂O₅Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 3h;solid phase reaction;	General procedure: Fmoc-protected amino acids were coupled using 3 equiv of amino acid, 3 equiv of HOBt, and 6 equiv of DIC. Couplings were performed in dimethylformamide at 0.2 M with respect to the incoming Fmoc-protected amino acid. Couplings were allowed to proceed for a minimum of 2 h, and were assayed via ninhydrin test to verify competition. Once complete, the coupling reaction solution was drained, and the resin subjected to Fmoc deprotection. (Note: Fmoc and N-methyl amino acids are coupled according to the cycle above, however for subsequent coupling onto the secondary amino terminus, HOBt was substituted with HOAt and the coupling was allowed to proceed overnight).

Reference： [1]Tetrahedron,2012,vol. 68,p. 1029 - 1051

82
[ 2812-32-0 ]
Fmoc-Pro-NovaSyn TGT resin [ No CAS ]
[ 68858-20-8 ]
[ 71989-31-6 ]
[ 103478-58-6 ]
N,N-dimethyl-valyl-valyl-methyl-valyl-prolyl-proline [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 941 - 944

83
[ 71989-14-5 ]
[ 103478-58-6 ]
Fmoc-D-Tyr(O-tBu)-OH [ No CAS ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
H-Gly-(2-chlorotrityl resin) [ No CAS ]
[ 1360075-55-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The linear pentapeptide precursor of cyclic RGD peptide, H-Asp(OtBu)-D-Phe(p-Br)- Lys(Boc)-Arg(Pbf)-Gly-OH (2), were assembled on the commercially-available Gly-preloaded 2-chlorotrityl resin (substitution: 0.74 mmol/g resins, Watanabe Chemical, Japan). The resin (50 mg, 0.037 mmol) was swelled in DMF for 2 h before use. Fmoc-amino acid (0.185 mmol (5 equiv)), coupling reagent (HBTU or COMU, 0.185 mmol (5 equiv)) and DIEA (0.37 mmol, 10 equiv) were added to the resin and the mixture was reacted for 10 min under MW irradiation (200W, 50 oC). The resin was washed with DMF (4 times). Deprotection of Fmoc group was carried out by treatment of 20% piperidine/DMF for 3 min under MW irradiation (200W, 50oC). The resulted peptidyl resin was treated with CH2Cl2-CF3CH2OH-AcOH (4:1:1 (v/v/v), 5 ml) for 90 min at room temperature. The solution of the cleaved cyclic peptide was concentrated in vacuo. The residue was lyophilized to afford crude. The purity of the product was checked by reversed-phase HPLC.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1066 - 1070

84
[ 103478-58-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 1360075-54-2 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1066 - 1070

85
[ 2812-32-0 ]
Fmoc-Pro-NovaSyn TGT resin [ No CAS ]
[ 68858-20-8 ]
[ 71989-31-6 ]
[ 103478-58-6 ]
N,N-dimethylvalyl-valyl-N-methylvalyl-prolyl-proline [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 5887 - 5892

86
[ 861851-74-3 ]
[ 29022-11-5 ]
[ 71989-14-5 ]
[ 103478-58-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 1380421-53-3 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 5271 - 5278

87
C₁₆H₁₃ClN₂O₃ [ No CAS ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 103478-58-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₄₃H₆₅N₉O₁₁S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 5271 - 5278

88
[ 29022-11-5 ]
C₂₂H₂₃ClN₂O₅ [ No CAS ]
[ 35661-40-6 ]
[ 103478-58-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₄₃H₆₅N₉O₁₁S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 5271 - 5278

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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. 103478-58-6 ] {[proInfo.proName]}

Quality Control of [ 103478-58-6 ]

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Druglikeness

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Medicinal Chemistry

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Application In Synthesis of [ 103478-58-6 ]

[ 103478-58-6 ] Synthesis Path-Upstream 1~6

[ 103478-58-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 103478-58-6 ]

Amino Acid Derivatives

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Physical hazards

Health hazards

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[ 103478-58-6 ]