[ CAS No. 106719-44-2 ] {[proInfo.proName]}

Name: 106719-44-2|Boc-D-Lys-OH|97%
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Quality Control of [ 106719-44-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 106719-44-2 ]

SDS Specification

Alternatived Products of [ 106719-44-2 ]

Product Details of [ 106719-44-2 ]

CAS No. :	106719-44-2	MDL No. :	MFCD00076956
Formula :	C₁₁H₂₂N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DQUHYEDEGRNAFO-MRVPVSSYSA-N
M.W :	246.30	Pubchem ID :	7018770
Synonyms :		Chemical Name :	Boc-D-Lys-OH

Calculated chemistry of [ 106719-44-2 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	9
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	63.98
TPSA :	101.65 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	-1.59
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	0.61
Log Po/w (SILICOS-IT) :	0.29
Consensus Log Po/w :	0.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	0.23
Solubility :	417.0 mg/ml ; 1.69 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.04
Solubility :	227.0 mg/ml ; 0.921 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.52
Solubility :	7.44 mg/ml ; 0.0302 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.89

Safety of [ 106719-44-2 ]

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 [ 106719-44-2 ]

* 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 [ 106719-44-2 ]
Downstream synthetic route of [ 106719-44-2 ]

[ 106719-44-2 ] Synthesis Path-Upstream 1~7

1
[ 106719-44-2 ]
[ 501-53-1 ]
[ 55878-47-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 16.5 h;	N6-((benzyloxy)carbonyl)-N2-(tert-butoxycarbonyl)-D-lysine (29) To a 1M aqueous solution of NaOH (37 mLat rt were added Z-D-Lys(Boc)-OH (3.00 g, 12.2) and dioxane slowly until the suspension dissolves. Then benzyl chloroformate was added (2.70 g, 2.3 15.9) dropwise over a period of 30 min at 0 C. The reaction mixture was stirred for 16 h at room temperature. Furthermore dioxane was removed in vacuo and reaction mixture was acidified to pH 2 with 1M HCl at 0 C. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na₂S0₄, filtered and evaporated in vacuo to afford compound 29 (4.4, 11.6 mmol, 95percent) as a white foam. No further purification was required. 1H-NMR (360 MHz, CDC1₃): δ (ppm) 7.37-7.23 (m, 5H), 6.18 (br s, 1H), 5.17- 4.86 (m, 3H), 4.83 (s, 1H), 4.22-4.04 (m, 1H), 3.13-3.11 (m, 2H), 1.76-1.37 (m, 15H). ¹³C- NMR (150 MHz, CDC1₃): δ (ppm) 176.4 (CO), 156.8 (CO), 156.0 (CO), 136.6 (C_q), 128.7 (2 x CH), 128.3 (2 x CH), 128.1 (CH), 80.4 (C_q) 66.9 (CH₂), 53.3 (CH), 40.7 (CH₂), 32.0 (CH₂), 29.3 (CH₂), 29.5 (3 x CH₃), 22.1 (CH₂). MS (ESI) m/z (percent): (Ci₄H₂oN₂0₄) 222 (14), (C₇Hi₂N0₄) 174 (12), 128 (32), 108 (27), 92 (11), (C₇H₇) 91 (100), 84 (20), 57 (52), 41 (20). MS (ESI) m/z calcd for Ci4H₂oN₂0₄ [M + H - C₅H₉0₂]⁺, 280.14; found 280.14. LC-MS (ESI) m/z calcd. for Ci9H₂₈N₂0₆Na [M+Na]⁺, 403.2; found, 403.7. HPLC purity, 96percent, t_R = 19.7 min, gradient A.

Reference： [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 2222 - 2243
[2] Patent: WO2017/63910, 2017, A1, . Location in patent: Page/Page column 38-39

2
[ 55878-47-2 ]
[ 106719-44-2 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1991, # 5, p. 914 - 934
[2] Journal of the American Chemical Society, 2014, vol. 136, # 31, p. 10874 - 10877

3
[ 24424-99-5 ]
[ 106719-44-2 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1991, # 5, p. 914 - 934

4
[ 34404-32-5 ]
[ 106719-44-2 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1991, # 5, p. 914 - 934

5
[ 7274-88-6 ]
[ 106719-44-2 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1991, # 5, p. 914 - 934

6
[ 106326-22-1 ]
[ 106719-44-2 ]

Reference： [1] Journal of the American Chemical Society, 2014, vol. 136, # 31, p. 10874 - 10877

7
[ 28920-43-6 ]
[ 106719-44-2 ]
[ 115186-31-7 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 27, p. 5427 - 5439

[ 106719-44-2 ] Synthesis Path-Downstream 1~88

1
[ 24690-42-4 ]
[ 106719-44-2 ]
[ 122546-52-5 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 914 - 934

2
[ 55878-47-2 ]
[ 106719-44-2 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 914 - 934
[2]Journal of the American Chemical Society,2014,vol. 136,p. 10874 - 10877

3
[ 106719-44-2 ]
[ 141789-87-9 ]
[ 135741-41-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2928 - 2931

4
[ 106719-44-2 ]
[ 74104-89-5 ]
[ 122532-81-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 636 - 640

5
[ 2208-07-3 ]
[ 106719-44-2 ]
(R)-6-Acetimidoylamino-2-tert-butoxycarbonylamino-hexanoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3886 - 3888

6
[ 106719-44-2 ]
[ 614-68-6 ]
[ 166898-11-9 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

7
[ 106719-44-2 ]
[ 106691-72-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 4; Synthesis of D-Boc-a-amino-e-caprolactam; In a 1L round bottom flask under a nitrogen atmosphere is placed 20 g (80 mmol) of N-a-Boc-D-lysine with 300 mL of DMF and a magnetic stir bar. 36 g of BOP is added to the room temperature slurry. The reaction is stirred for 15 minutes until clear. Then 36 g of NaHCO3 and 100 mL of DMF are added. After 20 hours, the reaction mixture is concentrated under vacuum. The concentrated mixture is diluted with water and aqueous NaHCO3 solution (1: 1) and extracted three times with ethyl acetate. The combined organic extracts are washed with water, saturated aqueous NaHCO3 solution, saturated aqueous NaCl solution, dried (Na2SO4), filtered and concentrated to afford a residue. The residue is triturated with ether (20 mL) and filtered. Washing the precipitate with hexanes led to another crop in the filtrate. A final crop is obtained by concentrating of the second filtrate and treatment with hexanes. Combining all crops affords the desired cyclized product. MS: 229 (M+H).

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4193 - 4201
[2]Patent: WO2005/42489,2005,A1 .Location in patent: Page/Page column 97
[3]Journal of Natural Products,2017,vol. 80,p. 2845 - 2849

8
[ 28920-43-6 ]
[ 106719-44-2 ]
[ 115186-31-7 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5427 - 5439

9
[ 117-08-8 ]
[ 106719-44-2 ]
C₁₉H₂₀Cl₄N₂O₆ [ No CAS ]

Reference： [1]Synlett,2006,p. 2743 - 2746

10
[ 106719-44-2 ]
2-[tert-butoxycarbonyl]amino-6-[(pyridin-2-yl)methyl]amino-1-hexanoic acid [ No CAS ]

Reference： [1]Synthesis,2004,p. 1759 - 1766

11
[ 106719-44-2 ]
6-(bis-pyridin-2-ylmethyl-amino)-2-tert-butoxycarbonylamino-hexanoic acid [ No CAS ]

Reference： [1]Synthesis,2004,p. 1759 - 1766
[2]Synthesis,2004,p. 1759 - 1766
[3]Synthesis,2004,p. 1759 - 1766

12
[ 106719-44-2 ]
2-[tert-butoxycarbonyl]amino-6-[(pyridin-2-yl)methyl,(thiazol-2-yl)methyl]amino-1-hexanoic acid [ No CAS ]

Reference： [1]Synthesis,2004,p. 1759 - 1766

13
[ 106719-44-2 ]
2-[tert-butoxycarbonyl]amino-6-[(1-methyl-1H-imidazol-2-yl)methyl,(thiazol-2-yl)methyl]amino-1-hexanoic acid [ No CAS ]

Reference： [1]Synthesis,2004,p. 1759 - 1766

14
[ 106719-44-2 ]
(R)-N^ε-stearoyl-lysine-thioethyl-ester [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 1782 - 1794

15
[ 106719-44-2 ]
2-tert-butoxycarbonylamino-6-octadecanoylamino-hexanethioic acid S-ethyl ester [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 1782 - 1794

16
[ 106719-44-2 ]
C₂₆H₁₇⁽²⁾H₃₅N₂O₂S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 1782 - 1794

17
[ 106719-44-2 ]
C₃₁H₂₅⁽²⁾H₃₅N₂O₄S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 1782 - 1794

18
[ 106719-44-2 ]
[ 78444-83-4 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4193 - 4201

19
[ 106719-44-2 ]
[ 250682-53-2 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 4193 - 4201

20
[ 106719-44-2 ]
D-N⁶-(1-iminoethyl)lysine dihydrochloride [ No CAS ]

Reference： [1]European Journal of Pharmacology,1995,vol. 273,p. 15 - 24
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 3886 - 3888

21
[ 106719-44-2 ]
[ 166446-81-7 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

22
[ 106719-44-2 ]
[ 736907-53-2 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

23
[ 106719-44-2 ]
[ 767263-51-4 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

24
[ 106719-44-2 ]
[ 167980-80-5 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

25
[ 106719-44-2 ]
[ 167980-81-6 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

26
[ 106719-44-2 ]
N-<1-<<<2-(R)-<<(adamantan-2-yloxy)carbonyl>amino>-3-(1H-indol-3-yl)-2-(R)-methylpropionyl>amino>methyl>5-(3-o-tolylureido)pentyl>succinamic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

27
[ 106719-44-2 ]
N-<1-<<<2-(R)-<<(adamantan-2-yloxy)carbonyl>amino>-3-(1H-indol-3-yl)-2-(S)-methylpropionyl>amino>methyl>5-(3-o-tolylureido)pentyl>succinamic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

28
[ 106719-44-2 ]
[ 166446-73-7 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

29
[ 106719-44-2 ]
[ 166446-75-9 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

30
[ 106719-44-2 ]
[ 167980-57-6 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3384 - 3390

31
[ 106719-44-2 ]
[ 139004-99-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2928 - 2931

32
[ 24424-99-5 ]
[ 106719-44-2 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 914 - 934

33
[ 34404-32-5 ]
[ 106719-44-2 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 914 - 934

34
[ 7274-88-6 ]
[ 106719-44-2 ]

Reference： [1]Journal of Chemical Research, Miniprint,1991,p. 914 - 934

35
[ 106719-44-2 ]
(R)-3-aminoazepan-2-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1; Synthesis of D-Boc-alpha-amino-epsilon-caprolactam; In a IL round bottom flask under a nitrogen atmosphere is placed 20 g (80 mmol) of N-alpha-Boc-D-lysine with 300 mL of DMF and a magnetic stir bar. 36 g of BOP is added to the room temperature slurry. The reaction is stirred for 15 minutes until clear. Then 36 g of NaHCO3 and 100 mL of DMF are added. After 20 hours, the reaction mixture is concentrated under vacuum. The concentrated mixture is diluted with water and aqueous NaHCO3 solution (1:1) and extracted three times with ethyl acetate. The combined organic extracts are washed with water, saturated aqueous NaHCO3 solution, saturated aqueous NaCl solution, dried (Na2SO4), filtered and concentrated to afford a residue. The residue is triturated with ether (20 mL) and filtered. Washing the precipitate with hexanes led to another crop in the filtrate. A final crop is obtained by concentrating of the second filtrate and treatment with hexanes. Combining all crops affords the desired cyclized product. MS: 229 (M+H); Procedure for synthesis of D-alpha-amino-epsilon-caprolactam HCl; The D-Boc-alpha-amino-epsilon-caprolactam (12 g, 52 mmol) is mixed with 130 mL of dioxane to form a cloudy solution. 30 mL of 4N HCl in dioxane is added and gas evolution is noted. After 2 hours, HPLC-MS shows incomplete reaction. Methanol (20 mL) and an additional 20 mL of 4N HCl in dioxane solution are added and stirring continued overnight. The resulting EPO <DP n="79"/>solid was filtered and dried in a vacuum oven to yield 8.85 g of the desired product. Chiral HPLC analysis showed no racemization. MS: 129 (M+H).

Reference： [1]Patent: WO2006/78753,2006,A1 .Location in patent: Page/Page column 77-78

Yield	Reaction Conditions	Operation in experiment
		Steps 1 through 13 were then repeated employing the following sequence of amino acids: Boc--D--Trp Boc--D--Trp Boc--Tyr(BrZ*) Boc--D--Lys(Z+)

37
Os₃(CO)10(HCC(CH₂)2C(O)ONC₄H₄O₂) [ No CAS ]
[ 106719-44-2 ]
Os3(CO)10[μ3-η(2)-HCC(CH2)2C(O)N(H)(CH2)4CH(NHCOOCMe3)(COOH)] [ No CAS ]

Reference： [1]Organometallics,1996,vol. 15,p. 3037 - 3041

38
[Ru(2,2'-bipyridine)2(C₁₆H₁₃N₃O₃)](hexafluorophosphate)3 [ No CAS ]
[ 106719-44-2 ]
[Ru(2,2'-bipyridine)2(N(α)-tert-butyloxycarbonyl-N(ω)-4-carbonyl-4'-methyl-2,2'-bipyridyl)-L-lysine](hexafluorophosphate)2 [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,1998,p. 957 - 963

39
[ 106719-44-2 ]
[ 152120-55-3 ]
[ 186369-16-4 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 1509 - 1516

40
[ 858104-55-9 ]
[ 106719-44-2 ]
C₃₈H₄₂F₂N₄O₉S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 10 iV6.(iV-[4.((2R,3R)-l-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4- 15 oxoazetidin-2-yl)phenoxy]acetyI}gIycyl)-D-lysineTo a 30 0C solution of N-[4-((2i?,3i?)-l-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2- oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine (0.030g, 0.055 mmol) in CH2Cl220 (5 ml) under an atmosphere of nitrogen was added N-methylmorpholine (0.017 g, 0.166 mmol) followed by the addition of TBTU (0.023 g, 0.072 mmol). After 1.5h N2-{tert- butoxycarbonyl)-D-lysine (0.027 g, 0.111 mmol) was added. After 30 minutes full conversion to the corresponding amide had been obtained. The mixture was concentrated and the residue was purified through preparative HPLC using an eluent of 0-50% CH3CN in 0.1M NH4OAc25 buffer. Pure fractions were concentrated. To the residue was added trifluoroacetic acid (4 ml) and CH2Cl2 (2 ml). After 10 minutes, full deprotection of the Boc protective group had been achieved. The mixture was concentrated and to the residue was added MeOH (3 ml) and NaBH4 (0.010 g, 0.277 mmol). Full conversion to the desired alcohol had been obtained within 5 minutes. The mixture was purified through preparative HPLC using an eluent of 20-30 50% CH3CN in 0.1M NH4OAc as eluent. Freeze drying of pure fractions afforded the desired compound. 1H NMR [(CD3)2SO), 400 MHz] deltal.26-1.73 (m, 6H), 2.85-3.09 (m, 5H), 3.70 (d, 2H), 4.25-4.28 (m, IH), 4.53 (s, 2H), 4.68-4.75 (m, IH), 5.04-5.07 (m, IH), 6.97-7.38 (m, 12H), 7.87 (t, IH), 8.30 (t, IH).

Reference： [1]Patent: WO2006/137795,2006,A1 .Location in patent: Page/Page column 64

41
[ 132178-37-1 ]
[ 106719-44-2 ]
[ 1316670-21-9 ]

Reference： [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6793 - 6798

42
[ 106719-44-2 ]
[ 1316670-35-5 ]

Reference： [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6793 - 6798

43
[ 106719-44-2 ]
C₂₇H₃₉N₇O₅*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6793 - 6798

44
[ 106719-44-2 ]
C₂₇H₃₉N₇O₅*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6793 - 6798

45
[ 106719-44-2 ]
[ 1316670-54-8 ]

Reference： [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6793 - 6798

46
[ 106719-44-2 ]
[ 1316670-60-6 ]

Reference： [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6793 - 6798

47
[ 3326-32-7 ]
[ 106719-44-2 ]
C₂₇H₂₅N₃O₇S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12519 - 12523
Angew. Chem.,2012,vol. 124,p. 12687 - 12691,5

48
[ 3326-32-7 ]
[ 106719-44-2 ]
C₃₂H₃₃N₃O₉S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12519 - 12523
Angew. Chem.,2012,vol. 124,p. 12687 - 12691,5

49
[ 106719-44-2 ]
5-carboxy-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate [ No CAS ]
C₃₆H₄₂N₄O₈ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12519 - 12523
Angew. Chem.,2012,vol. 124,p. 12687 - 12691,5

50
[ 106719-44-2 ]
5-carboxy-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate [ No CAS ]
[ 1417905-39-5 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12519 - 12523
Angew. Chem.,2012,vol. 124,p. 12687 - 12691,5

51
[ 1426811-58-6 ]
[ 106719-44-2 ]
C₃₁H₅₀BN₃O₅ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2013,vol. 81,p. 408 - 413

52
[ 1426811-59-7 ]
[ 106719-44-2 ]
C₃₀H₄₈BN₃O₅ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2013,vol. 81,p. 408 - 413

53
[ 1426811-61-1 ]
[ 106719-44-2 ]
[ 1447170-38-8 ]

Reference： [1]Chemical Biology and Drug Design,2013,vol. 81,p. 408 - 413

54
[ 106719-44-2 ]
[ 152120-54-2 ]
(R)-6-[2,3-bis(tert-butoxycarbonyl)guanidino]-2-[(tert-butoxycarbonyl)amino]hexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In dichloromethane; at 20℃; for 16h;	Preparation of (R)-6-[2,3-bis(tert-butoxycarbonyl)guanidino]-2-[(tert-butoxycarbonyl)amino]hexanoic acid (8) A solution of N-alpha-Boc-D-lysine 12 (10.0 g, 40.6 mmol) in CH2Cl2 (200 mL) was charged with N,N'-bis-Boc-1-guanylpyrazole (11.3 g, 36.6 mmol) and triethylamine (11.0 mL, 81.3 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was washed with 10% aqueous citric acid (2100 mL) and the solvent was removed under reduced pressure. The residue was dissolved in 1 N NaOH (300 mL), 1 N HCl was added to adjust the pH to 5-6, and the mixture was extracted with CH2Cl2 (500 ml). The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (2250 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford compound 8 (18.5 g, 94%) as a white solid: 1H NMR (400 MHz, CD3OD) delta 4.13-4.03 (m, 1H), 3.36 (t, J=6.8 Hz, 2H), 1.91-1.77 (m, 1H), 1.74-1.55 (m, 3H), 1.52 (s, 9H), 1.51-1.38 (m, 2H), 1.47 (s, 9H), 1.43 (s, 9H).
22 g		To a solution of N-alpha-Boc-D-lysine (13.0 g, 52.7 mmol) in EtOH (290 mL) was added N,N'-bis-Boc-1-guanylpyrazole (16.3 g, 52.7 mmol) and triethyl amine (10.6 g, 105 mmol). The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was purified by column chromatography (silica gel, 10:1 CH2Cl2/MeOH) to afford a pyrazole salt (25.0 g) as colorless oil. _The salt was dissolved in 1 N NaOH (300 mL) and neutralized with 1 N HCl (305 mL) The resulting precipitate was filtered out and dried, to afford compound 3 (22.0 g, 85%) as a white solid: 1H NMR (400 MHz, CDCl3) delta 11.48 (br s, 1H), 8.35 (br s, 1H), 5.23 (d, J=7.5 Hz, 1H), 4.23 (br s, 1H), 3.48-3.25 (m, 2H), 1.96-1.50 (m, 6H), 1.51 (s, 9H), 1.49 (s, 9H), 1.43 (s, 9H).

Reference： [1]Patent: US2015/56305,2015,A1 .Location in patent: Paragraph 0284; 0286
[2]Patent: US2013/324559,2013,A1 .Location in patent: Paragraph 0475; 0476

55
C₁₉H₂₉BNO₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]
[ 106719-44-2 ]
C₂₇H₄₄BN₄O₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Reference： [1]Journal of Peptide Science,2013,vol. 19,p. 613 - 618

56
[ 1616668-55-3 ]
[ 106719-44-2 ]
N2-(tert-butoxycarbonyl)-N6-(tetrazine)-L-lysine [ No CAS ]

Reference： [1]ChemistryOpen,2014,vol. 3,p. 48 - 53

57
[ 75-09-2 ]
[ 1616668-55-3 ]
[ 106719-44-2 ]
methyl N2-(tert-butoxycarbonyl)-N6-(tetrazine)-L-lysinate [ No CAS ]

Reference： [1]ChemistryOpen,2014,vol. 3,p. 48 - 53

58
[ 106326-22-1 ]
[ 106719-44-2 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 10874 - 10877

59
[ 106719-44-2 ]
FDL-NH₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 10874 - 10877

60
[ 3326-32-7 ]
[ 106719-44-2 ]
Boc-FDL-NH₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 10874 - 10877

61
[ 106719-44-2 ]
(12R,19R)-methyl 6,12,19-tris[(tert-butoxycarbonyl)amino]-2,2-dimethyl-4,13-dioxo-3-oxa-5,7,14-triazaicos-5-en-20-oate [ No CAS ]

Reference： [1]Patent: US2015/56305,2015,A1
[2]Patent: US2015/56305,2015,A1

62
[ 106719-44-2 ]
(R)-2-amino-N-((R)-5-amino-6-(2-(1,4-dihydrobenzo[d][1,2]dithiin-6-yloxy)ethylamino)-6-oxohexyl)-6-guanidinohexanamide [ No CAS ]

Reference： [1]Patent: US2015/56305,2015,A1
[2]Patent: US2015/56305,2015,A1

63
[ 106719-44-2 ]
C₃₆H₅₇N₅O₁₀S₂ [ No CAS ]

Reference： [1]Patent: US2015/56305,2015,A1

64
[ 106719-44-2 ]
C₄₇H₇₇N₇O₁₃S₂ [ No CAS ]

Reference： [1]Patent: US2015/56305,2015,A1
[2]Patent: US2015/56305,2015,A1

65
[ 106719-44-2 ]
C₂₃H₄₁N₇O₃S₂*3ClH [ No CAS ]

Reference： [1]Patent: US2015/56305,2015,A1
[2]Patent: US2015/56305,2015,A1

66
[ 106719-44-2 ]
C₆₀H₁₀₀N₁₀O₁₈S₂ [ No CAS ]

Reference： [1]Patent: US2015/56305,2015,A1

67
[ 106719-44-2 ]
(12R,19R)-6,12,19-tris[(tert-butoxycarbonyl)amino]-2,2-dimethyl-4,13-dioxo-3-oxa-5,7,14-triazaicos-5-en-20-oic acid [ No CAS ]

Reference： [1]Patent: US2015/56305,2015,A1
[2]Patent: US2015/56305,2015,A1

68
[ 106719-44-2 ]
[ 18107-18-1 ]
[ 55757-60-3 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; hexane; dichloromethane; at 0 - 20℃; for 2h;	A solution of N-alpha-Boc-D-lysine 12 (1.00 g, 4.06 mmol) in CH2Cl2 (20 mL) and MeOH (5.0 mL) was charged with TMS-diazomethane [(CH3)3SiCHN2 0.6 M solution in hexane, 13.5 mL, 8.12 mmol] at 0 C. and stirred at the same temperature for 1 h and at room temperature for another 1 h. The solvent was removed under reduced pressure to afford crude product 14 (1.04 g, crude) as a yellow oil, which was directly used for the next step without further purification: 1H NMR (400 MHz, CD3OD) delta 4.12-4.05 (m, 1H), 3.70 (s, 3H), 2.62 (t, J=7.0 Hz, 2H), 1.82-1.70 (m, 1H), 1.69-1.58 (m, 1H), 1.54-1.32 (m, 4H), 1.43 (s, 9H).
	In methanol; hexane; dichloromethane; at 20℃; for 0.833333h;	BOC-D-LYS-OH 4a (8 g, 32 5 mmol) was dissolved in dichloromethane/methanol (10: 1, 110 mL). TMS-Diazomethane (2M in hexanes, 20 mL, 40 mmol) was added dropwise and the reaction mixture was stirred for 50 minutes at room temperature. The reaction was quenched with dropwise addition of acetic acid until the reaction mixture became colorless. The reaction was then concentrated and carried forward without purification.

Reference： [1]Patent: US2015/56305,2015,A1 .Location in patent: Paragraph 0285; 0286
[2]Patent: WO2018/93695,2018,A1 .Location in patent: Page/Page column 25-26

69
[ 106719-44-2 ]
C₁₃H₁₇N₅O₅ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 6158 - 6162
Angew. Chem.,2015,vol. 127,p. 6256 - 6260,5

70
[ 106719-44-2 ]
C₁₄H₁₉N₅O₅ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 6158 - 6162
Angew. Chem.,2015,vol. 127,p. 6256 - 6260,5

71
[ 106719-44-2 ]
C₁₂H₁₅N₅O₅ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 6158 - 6162
Angew. Chem.,2015,vol. 127,p. 6256 - 6260,5

72
[ 106719-44-2 ]
[ 10199-89-0 ]
C₁₇H₂₃N₅O₇ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 6158 - 6162
Angew. Chem.,2015,vol. 127,p. 6256 - 6260,5

73
[ 109856-85-1 ]
[ 106719-44-2 ]
C₃₅H₇₀N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; for 192h;	[00216j Synthesis of compound 12.1: A mixture of N-Boc-D-Lysine 11.1 (49.2 g, 0.2 mole) and the epoxide 5.1 (147.2 g, 0.8 mole) in MeOH (1.04 L) was stirred at room temperature. DIPEA (51.9 g, 0.4 mole) was added. The resulting mixture was then stirred for 8 days, and then concentrated to dryness. The residue was purified on a silica gel column (2 kg, MeOH/DCM, 0 to 10%) to give 49.2 g of mostly pure 12.1 (MZ-550-180) and 58.3 g of impure 12.1, which was purified by a second column (1.5 kg, MeOH/EtOAc, 10 to 40%) to give 41.4 g of mostly pure 12.1. The two mostly pure batches were combined and stirred with EtOAc (0.5 L) for 3 h. The mixture was filtered to give 41.4 g pure 12.1 as a white solid. The filtrate was concentrated to dryness. The residue was stirred with EtOAc (0.1 L) for lh and filtered to give 10.6 g of pure 12.1. The filtrate was concentrated to dryness and the residue was purified on a silica gel column (330 g, MeOH/EtOAc, 10 to 40%) to give a third batch of 26.9 g pure 12.1. Atotal of 78.9 g of pure 12.1 was obtained. Yield: 64%

Reference： [1]Patent: WO2015/200465,2015,A1 .Location in patent: Paragraph 00191; 00216

74
[ 106719-44-2 ]
[ 130404-09-0 ]
C₃₅H₇₀N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine; In methanol; at 20℃; for 168h;	[00206j Synthesis of compound 10.2: To a suspension of 11.1, Boc-D-lysine (14 g, 0.057 mol) in MeOH (900 mL) were added TEA (11.6 mL) and 5.2 (42 g, 0.228 mol). The mixture was stirred at room temperature for 7 days. Volatiles were removed and the crude product was purified by column (1.0 kg of 5i02, eluted with 0 - 40% MeOH in EtOAc) to give 24 g (70%) of pure compound 10.2.

Reference： [1]Patent: WO2015/200465,2015,A1 .Location in patent: Paragraph 00200; 00206

75
[ 106719-44-2 ]
[ 501-53-1 ]
[ 55878-47-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 16.5h;	N6-((benzyloxy)carbonyl)-N2-(tert-butoxycarbonyl)-D-lysine (29) To a 1M aqueous solution of NaOH (37 mLat rt were added Z-D-Lys(Boc)-OH (3.00 g, 12.2) and dioxane slowly until the suspension dissolves. Then benzyl chloroformate was added (2.70 g, 2.3 15.9) dropwise over a period of 30 min at 0 C. The reaction mixture was stirred for 16 h at room temperature. Furthermore dioxane was removed in vacuo and reaction mixture was acidified to pH 2 with 1M HCl at 0 C. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2S04, filtered and evaporated in vacuo to afford compound 29 (4.4, 11.6 mmol, 95%) as a white foam. No further purification was required. 1H-NMR (360 MHz, CDC13): delta (ppm) 7.37-7.23 (m, 5H), 6.18 (br s, 1H), 5.17- 4.86 (m, 3H), 4.83 (s, 1H), 4.22-4.04 (m, 1H), 3.13-3.11 (m, 2H), 1.76-1.37 (m, 15H). 13C- NMR (150 MHz, CDC13): delta (ppm) 176.4 (CO), 156.8 (CO), 156.0 (CO), 136.6 (Cq), 128.7 (2 x CH), 128.3 (2 x CH), 128.1 (CH), 80.4 (Cq) 66.9 (CH2), 53.3 (CH), 40.7 (CH2), 32.0 (CH2), 29.3 (CH2), 29.5 (3 x CH3), 22.1 (CH2). MS (ESI) m/z (%): (Ci4H2oN204) 222 (14), (C7Hi2N04) 174 (12), 128 (32), 108 (27), 92 (11), (C7H7) 91 (100), 84 (20), 57 (52), 41 (20). MS (ESI) m/z calcd for Ci4H2oN204 [M + H - C5H902]+, 280.14; found 280.14. LC-MS (ESI) m/z calcd. for Ci9H28N206Na [M+Na]+, 403.2; found, 403.7. HPLC purity, 96%, tR = 19.7 min, gradient A.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2222 - 2243
[2]Patent: WO2017/63910,2017,A1 .Location in patent: Page/Page column 38-39

76
[ 106719-44-2 ]
benzyl tert-butyl-{6-[(2,2-diphenylethyl)amino]-6-oxohexane-1,5-diyl}-(R)-dicarbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2222 - 2243

77
[ 106719-44-2 ]
tert-butyl (R)-{6-amino-1-[(2,2-diphenylethyl)amino]-1-oxohexan-2-yl}carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2222 - 2243

78
[ 106719-44-2 ]
benzyl (S)-3-[(R)-5-((tert-butoxycarbonyl)amino)-6-((2,2-diphenylethyl)amino)-6-oxohexyl]carbamoyl}-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2222 - 2243

79
[ 106719-44-2 ]
tert-butyl {(R)-1-[(2,2-diphenylethyl)amino]-1-oxo-6-[(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido]hexan-2-yl}-carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2222 - 2243

80
[ 106719-44-2 ]
tert-butyl {(R)-1-[(2,2-diphenylethyl)amino]-1-oxo-6-[(S)-2-(4-oxo-4-phenylbutanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido]hexan-2-yl}carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2222 - 2243

81
[ 106719-44-2 ]
(R)-1-((2,2-diphenylethyl)amino)-1-oxo-6-((S)-2-(4-oxo-4-phenylbutanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)hexan-2-aminium 2,2,2-trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2222 - 2243

82
[ 106719-44-2 ]
[ 76-05-1 ]
[ 74-88-4 ]
(R)-5-amino-5-carboxy-N,N,N-trimethylpentan-1-aminium 2,2,2-trifluoroacetate [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 12849 - 12852

83
[ 106719-44-2 ]
D-α-amino-ε-caprolactam trifluoroacetate [ No CAS ]

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 2845 - 2849

84
[ 106719-44-2 ]
[ 1067658-96-1 ]

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 2845 - 2849

85
[ 106719-44-2 ]
(x)C₂HF₃O₂*C₁₆H₂₃N₃O₂ [ No CAS ]

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 2845 - 2849

86
[ 106719-44-2 ]
[ 1067659-02-2 ]

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 2845 - 2849

87
[ 106719-44-2 ]
(x)C₂HF₃O₂*C₁₆H₂₃N₃O₂ [ No CAS ]

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 2845 - 2849

88
[ 38862-24-7 ]
[ 106719-44-2 ]
Nα-Boc-Nε-acryloyl-D-lysine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4528 - 4560

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Ghs Precautionary Statements

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Code	Phrase
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P321
P322
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P342	If experiencing respiratory symptoms:
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P378
P380	Evacuate area.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P370 + P376	In case of fire: Stop leak if safe to Do so.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 106719-44-2 ] {[proInfo.proName]}

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[ 106719-44-2 ] Synthesis Path-Upstream 1~7

[ 106719-44-2 ] Synthesis Path-Downstream 1~88

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Amino Acid Derivatives

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[ 106719-44-2 ]