[ CAS No. 127474-54-8 ] {[proInfo.proName]}

Name: 127474-54-8|(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid|97%
Brand: Ambeed
SKU: A298801
Price: 5.0 USD
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2D 3D

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Quality Control of [ 127474-54-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 127474-54-8 ]

SDS Specification

Alternatived Products of [ 127474-54-8 ]

Product Details of [ 127474-54-8 ]

CAS No. :	127474-54-8	MDL No. :	MFCD02094549
Formula :	C₁₃H₁₅NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DGEZDWGCGXHLEW-LLVKDONJSA-N
M.W :	249.26	Pubchem ID :	10243780
Synonyms :

Calculated chemistry of [ 127474-54-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.23
Num. rotatable bonds :	8
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	66.02
TPSA :	75.63 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) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.17
Log Po/w (WLOGP) :	1.79
Log Po/w (MLOGP) :	1.62
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.47
Solubility :	0.842 mg/ml ; 0.00338 mol/l
Class :	Soluble
Log S (Ali) :	-3.39
Solubility :	0.101 mg/ml ; 0.000406 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.82
Solubility :	0.376 mg/ml ; 0.00151 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.94

Safety of [ 127474-54-8 ]

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

Application In Synthesis of [ 127474-54-8 ]

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

Upstream synthesis route of [ 127474-54-8 ]
Downstream synthetic route of [ 127474-54-8 ]

[ 127474-54-8 ] Synthesis Path-Upstream 1~3

1
[ 133773-64-5 ]
[ 16338-48-0 ]
[ 127474-54-8 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 84, p. 22 - 26

2
[ 1069-48-3 ]
[ 16338-48-0 ]
[ 127474-54-8 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 84, p. 22 - 26

3
[ 50299-14-4 ]
[ 501-53-1 ]
[ 78553-51-2 ]
[ 127474-54-8 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 3, p. 717 - 728

[ 127474-54-8 ] Synthesis Path-Downstream 1~61

1
[ 186581-53-3 ]
[ 127474-54-8 ]
[ 127515-28-0 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 1243 - 1264

2
[ 67-56-1 ]
[ 127474-54-8 ]
[ 127515-28-0 ]

Reference： [1]Organic Process Research and Development,2002,vol. 6,p. 762 - 766
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6286 - 6294
[3]Tetrahedron,2004,vol. 60,p. 717 - 728

3
[ 54594-06-8 ]
[ 501-53-1 ]
[ 127474-54-8 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 1243 - 1264
[2]Journal of the American Chemical Society,2014,vol. 136,p. 10874 - 10877
[3]Journal of Organic Chemistry,1992,vol. 57,p. 6286 - 6294
[4]Organic and Biomolecular Chemistry,2015,vol. 13,p. 5997 - 6009

4
2-Benzyloxycarbonylamino-pent-4-enoic acid 2-chloro-ethyl ester [ No CAS ]
[ 78553-51-2 ]
[ 127474-54-8 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1988,p. 1214 - 1216

5
[ 565234-18-6 ]
[ 127474-54-8 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7679 - 7692
[2]Chemical Communications,2003,p. 468 - 469

6
[ 50299-14-4 ]
[ 501-53-1 ]
[ 78553-51-2 ]
[ 127474-54-8 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 717 - 728

7
[ 186581-53-3 ]
[ 67-56-1 ]
[ 127474-54-8 ]
[ 81576-71-8 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 3375 - 3382

8
[ 13139-17-8 ]
[ 54594-06-8 ]
[ 127474-54-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With water; triethylamine; In 1,4-dioxane; at 20℃;	To a suspension of D-2-amino-4-pentenoic acid (500 mg) in Dioxane (20 mL) at RT was added triethylamine (1.09 g), water (0. 5 mL), and N- (BENZYLOXYCARBONYLOXY) SUCCINIMIDE (2.27 g). The reaction mixture was stirred overnight at RT, concentrated in vacuo, diluted with saturated NAHCO3 and extracted with ether (3x). The basic aqueous layer was acidified to pH 2 with 2N HCI and extracted with EtOAc (3x). The combined EtOAc layer was washed with brine, dried (NA2S04), filtered and concentrated to give a clear viscous oil (1.17 g, quantitative). H NMR (300 MHz, DMSO-d6) 8 2.29-2. 50 (M, 2H), 3.98-4. 06 (M, 1H), 5.03 (s, 2H), 5.05-5. 12 (M, 2H), 5. 71-5. 84 (m, 1H), 7.35 (M, 5H), 7.54 (d, 1H), 12.57 (bs, 1H). MS APCI, m/z = 250 (M+1). LC/MS 1.90 min. , Method A.
76%	With triethylamine; In tetrahydrofuran; water; at 20℃;	D-allylglycine (2.07 g, 18.0 mmol) and N-(benzyloxycarbonyloxy)succinimide (Cbz-OSu) (4.49 g, 18.0 mmol) are added to a round bottomed flask containing THF (60 mL) and water (20 mL). The mixture is stirred at room temperature and Et3N (10.1 mL, 72.0 mmol) is added, and the reaction is stirred overnight at room temperature. The clear solution is diluted with EtOAc (200 mL), washed with IN HCl (3 x 100 mL) and brine (1 x 100 mL), and dried with MgSO4. Solvent is evaporated in vacuo to afford 10-B as a white solid, which is used without further purification.

Reference： [1]Patent: WO2004/80983,2004,A1 .Location in patent: Page 50, 51
[2]Patent: WO2008/97673,2008,A1 .Location in patent: Page/Page column 29-30
[3]Organic Letters,2006,vol. 8,p. 239 - 242

9
[ 875574-58-6 ]
[ 127474-54-8 ]
[ 875574-67-7 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 239 - 242

11
benzyl 1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-1-oxopent-4-en-2-ylcarbamate [ No CAS ]
[ 78553-51-2 ]
[ 127474-54-8 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3997 - 4000

12
2-bromo-N-(2,4-dimethoxybenzyl)prop-2-en-1-amine [ No CAS ]
[ 127474-54-8 ]
[ 781649-92-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	1- [3- (DIMETHYLAMINO) PROPYL]-3-ETHYLCARBODIIMIDE hydrochloride (55 mg, 0.285 mmol) was added to a solution of 2-bromo-N- (2, 4-dimethoxybenzyl) prop-2-en-1-amine (73 mg, 0.256 mmol) and (2R)-2-[(benzyloxy) carbonyl] amino} PENT-4-ENOIC acid (71 mg, 0.285 mmol) in dichloromethane (5 ML). After 18 h the mixture was concentrated. Purification by silica gel chromatography (5% ethyl ACETATE/HEXANES 30% ethyl acetate/hexanes) gave the title compound (77 mg). MS 517 (M+1).
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	Step B: Benzyl (1R)-1-[(2-bromoprop-2-enyl)(2,4-dimethoxybenzyl)amino]carbonyl}but-3-enylcarbamate 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (55 mg, 0.285 mmol) was added to a solution of 2-bromo-N-(2,4-dimethoxybenzyl)prop-2-en-1-amine (73 mg, 0.256 mmol) and <strong>[127474-54-8](2R)-2-[(benzyloxy)carbonyl]amino}pent-4-enoic acid</strong> (71 mg, 0.285 mmol) in dichloromethane (5 mL). After 18 h the mixture was concentrated. Purification by silica gel chromatography (5% ethyl acetate/hexanes?30% ethyl acetate/hexanes) gave the title compound (77 mg). MS 517 (M+1).
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	Step B: Benzyl (lR)-l"[(2-bromoprop-2-enyl)(2^-dimethoxybenzyl) amino]carbonyl\|but-3- enylcarbamate; l-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (55 mg, 0.285 mmol) was added to a solution of 2-bromo-N-(2,4-dimethoxybenzyl)prop-2-en-l -amine (73 mg, 0.256 mmol) and (2R)-2-[(benzyloxy)carbonyl] amino }pent-4-enoic acid (71 mg, 0.285 mmol) in dichloromethane (5 mL). After 18 h the mixture was concentrated. Purification by silica gel chromatography (5% ethyl acetate/ hexanes -> 30% ethyl acetate/ hexanes) gave the title compound (77 mg). MS 517 (M+l).

	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	l-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (55 mg, 0.285 mmol) was added to a solution of 2-bromo-N-(2,4-dimethoxybenzyl)prop-2-en-l -amine (73 mg, 0.256 mmol) and (2R)-2-[(benzyloxy)carbonyl] amino }pent-4-enoic acid (71 mg, 0.285 mmol) in dichloromethane (5 mL). After 18 h the mixture was concentrated. Purification by silica gel chromatography (5% ethyl acetate/ hexanes -> 30% ethyl acetate/ hexanes) gave the title compound (77 mg). MS 517 (M+l).
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	Step B. Benzyl (li?)-l-[(2-bromoprop-2-enyl)(2.4-dimethoxybenzyl) amino] carbonyllbut-3- enylcarbamate; l-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (55 mg, 0.285 mmol) was added to a solution of 2-bromo-N-(2,4-dimethoxybenzyl)prop-2-en-l -amine (73 mg, 0.256 mmol) and (2i?)-2-[(benzyloxy)carbonyl]amino}pent-4-enoic acid (71 mg, 0.285 mmol) in dichloromethane (5 mL). After 18 h the mixture was concentrated. Purification by silica gel chromatography (5% ethyl acetate/ hexanes - >? 30% ethyl acetate/ hexanes) gave the title compound (77 mg). MS 517 (M+l ).
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	l-[3-(Dimethylamino)propyl]-3-ethylcarbodiirnide hydrochloride (55 mg, 0.285 mmol) was added to a solution of 2-bromo-N-(2,4-dimethoxybenzyl)prop-2-en-l -amine (73 mg, 0.256 mmol) and (2i?)-2-[(benzyloxy)carbonyi]amino}pent-4-enoic acid (71 mg, 0.285 mmol) in dichloromethane (5 mL). After 18 h the mixture was concentrated. Purification by silica gel chromatography (5% ethyl acetate/ hexanes -» 30% ethyl acetate/ hexanes) gave the title compound (77 mg). MS 517 (M+l). EPO <DP n="57"/>

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5564 - 5567
[2]Patent: WO2004/92166,2004,A2 .Location in patent: Page 81
[3]Patent: US2007/287696,2007,A1 .Location in patent: Page/Page column 20
[4]Patent: WO2006/41830,2006,A2 .Location in patent: Page/Page column 62; 65
[5]Patent: WO2006/44449,2006,A2 .Location in patent: Page/Page column 54
[6]Patent: WO2006/44504,2006,A1 .Location in patent: Page/Page column 99
[7]Patent: WO2006/47196,2006,A2 .Location in patent: Page/Page column 55

13
[ 127474-54-8 ]
[ 875574-76-8 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 239 - 242

14
[ 127474-54-8 ]
(2R,5S)-methyl 2-allyl-3-oxooctahydroimidazo[1,2-a]pyridine-5-carboxylate hydrobromide [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 239 - 242

15
[ 127474-54-8 ]
[ 91280-45-4 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 3375 - 3382

16
[ 127474-54-8 ]
[ 290838-42-5 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 3375 - 3382

17
[ 127474-54-8 ]
[ 475291-71-5 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 3375 - 3382

18
[ 247050-08-4 ]
[ 127474-54-8 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7679 - 7692
[2]Chemical Communications,2003,p. 468 - 469

19
[ 565234-17-5 ]
[ 127474-54-8 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7679 - 7692
[2]Chemical Communications,2003,p. 468 - 469

20
[ 565234-16-4 ]
[ 127474-54-8 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7679 - 7692
[2]Chemical Communications,2003,p. 468 - 469

21
[ 565234-15-3 ]
[ 127474-54-8 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7679 - 7692
[2]Chemical Communications,2003,p. 468 - 469

22
[ 127474-54-8 ]
[ 475504-29-1 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 717 - 728
[2]Organic Process Research and Development,2002,vol. 6,p. 762 - 766

23
[ 144073-06-3 ]
[ 127474-54-8 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6286 - 6294

24
[ 127474-54-8 ]
[ 125773-34-4 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6286 - 6294

25
[ 127474-54-8 ]
[ 144072-87-7 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6286 - 6294

26
[ 144073-07-4 ]
[ 127474-54-8 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6286 - 6294

27
[ 127474-54-8 ]
[ 127474-53-7 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 1243 - 1264

28
[ 127474-54-8 ]
[ 127474-53-7 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 1243 - 1264

29
[ 127474-54-8 ]
[ 127474-52-6 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 1243 - 1264

30
[ 127474-54-8 ]
[ 127474-52-6 ]

Reference： [1]Il Farmaco,1991,vol. 46,p. 1243 - 1264

31
[ 86766-70-3 ]
[ 127474-54-8 ]
[ 762289-27-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;4-N,N-dimethylaminopyridine trifluoroacetate; In dichloromethane; at -20 - 20℃; for 5.5h;	To a solution of (2R)-2-[(benzyloxy) carbonyl] amino} pent-4-enoic acid (3a) (1.1 g) in DCM (5 mL) at-20C under N2 was added a mixture of EDAC. HCI (1.02 g) and DMAP (12 MG) in DCM (8 ML) portionwise. Methyl (1-PHENYLPROP-2-EN-1-YL) amine (LD) (650 mg) in DCM (3 mL) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1.5 h at-20C and 4 h at RT, then diluted with DCM (100mL) and WASHED WITH 0. 2 N HCI, saturated NAHCO3, brine, dried (Na2S04), filtered, and evaporated. The crude product was purified via flash chromatography (20% EtOAc/hexanes) to give the desired product as a viscous oil (1.04 g, 63%). 1H NMR (300 MHZ, CDC13) 8 2.38-2. 47 (M, 1H), 2.50-2. 59 (M, 1H), 2. 66- 2. 82 (M, 3H-diastereomer/rotamer mixture), 4.77-4. 80 (M, 1H), 5. 08-5. 17 (M, 4H), 5.22-5. 48 (M, 2H), 5.69-5. 82 (m9 2H), 6.03-6. 14 (M, 1H), 6.39-6. 43 (M9 IH), 7.25-7. 35 (M, 10H). MS APCI, m/z = 379 (M+1). LC/MS 2. 72 min., Method A

Reference： [1]Patent: WO2004/80983,2004,A1 .Location in patent: Page 50, 51-52

32
[ 127474-54-8 ]
[ 781649-92-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;	1- [3- (DIMETHYLAMINO) PROPYL]-3-ETHYLCARBODLIMIDE HYDROCHLORIDE (55 mg, 0.285 mmol) was added to a solution of 2-bromo-N- (2, 4-dimethoxybenzyl) prop-2-en-1-amine (73 mg, 0.256 mmol) and (2R)-2-[(benzyloxy) carbonyl] amino} pent-4-enoic acid (71 mg, 0.285 mmol) in dichloromethane (5 mL). After 18 h the mixture was concentrated. Purification by silica gel chromatography (5% ETHYL ACETATE/HEXANES-> 30% ethyl acetate/hexanes) gave the title compound (77 mg). MS 517 (M+1).

Reference： [1]Patent: WO2004/92166,2004,A2 .Location in patent: Page 95

33
[ 54594-06-8 ]
[ 127474-54-8 ]

Yield	Reaction Conditions	Operation in experiment
		(2R)-2-[(benzyloxy)carbonyl] amino }pent-4-enoic acid 42, prepared in one step from commercially available D-allyl glycine according to known procedures (J. Chem. Soc, 1962, 3963-3968),

Reference： [1]Patent: WO2006/41830,2006,A2 .Location in patent: Page/Page column 45

34
[ 3182-77-2 ]
[ 501-53-1 ]
[ 127474-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In tetrahydrofuran;	a (R)-2-[[(Phenylmethoxy)carbonyl]amino]-4-pentenoic acid A mixture of D-allylglycine (2.8 g, 24.3 mmol), 1 M aqueous sodium hydroxide solution (25 ml), and tetrahydrofuran (10 ml, distilled from ketyl) was stirred at room temperature until homogeneous then cooled in an ice-bath. To the resulting rapidly stirred solution was added about 5 mL of 1.0M aqueous sodium hydroxide solution then dropwise about 1 g of benzyl chloroformate. This was repeated 4 additional times until a total of 28 mL of 1.0M aqueous sodium hydroxide solution and 4.80 g (95%, 27 mmol) of benzyl chloroformate were added. The reaction mixture was stirred for 15 minutes at 0 C. then 30 minutes at room temperature and then extracted with 50 mL of ether. The aqueous layer was acidified (pH=1.5) the by addition of 6N hydrochloric acid solution (about 10 mL) then extracted with three-50 mL portions of ether. The three ether extracts were combined, dried (magnesium sulfate) and concentrated in vacuo to afford 6.01 g of title product as a colorless oil.

Reference： [1]Patent: US5508272,1996,A

35
[ 6638-79-5 ]
[ 127474-54-8 ]
[ 939411-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In dichloromethane; at 0 - 20℃; for 0.833333h;	Step 2: Benzyl (1R.2R)-l-hydroxy-l-phenylpent-4-en-2-ylcarbamate. To a mixture of HATU (0.915 g, 2.41 mmol), (R)-2-(benzyloxycarbonyl)pent-4- enoic acid (0.400 g, 1.60 mmol), N-methoxymethanamine hydrochloride (0.188 g, 1.93 mmol) in CH2Cl2 (20 mL) at 0 0C was added triethylamine (0.558 ml, 4.01 mmol). The mixture was allowed to stir at 0 0C for 20 min then warmed to RT for 30 min. The reaction was diluted with CH2Cl2 (20 mL) and washed with 1 M HCl (30 mL), 9%Na2CO3 (30 mL), brine (30 mL), dried over Na2SO4, filtered through a small plug of silica gel and washed with ether (10 mL) and concentrated. The crude material was used without further purification. MS m/z = 293 [M+l]+. Calc'd for Ci5H2ON2O4: 292. To a solution of (R)-benzyl l-(methoxy(methyl)amino)-l-oxopent-4-en-2- ylcarbamate (0.468 g, 1.60 mmol) in THF (10 mL) at 0 0C was added phenylmagnesium bromide (1.0 M in THF, 4.80 ml, 4.80 mmol). The mixture was allowed to warm to room temperature and stir overnight. To the mixture was added saturated aqueous NH4Cl (10 mL). The volatiles were removed under reduced pressure. The residue was diluted with water and extracted with Et2O (3 x 20 mL). The combined organics were washed with HCl (1 M, 20 mL), water (20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The crude was used without further purification. MS m/z = 310 [M+l]+. Calc'd for C19H19NO3: 309.To (R)-benzyl 1 -oxo-1 -phenylpent-4-en-2-ylcarbamate (2.13 g, 6.89 mmol) in THF (50 mL) at -78 0C under argon was added lithium tri-sec-butylborohydride (20.7 ml, 20.7 mmol). Allowed the mixture to stir for 45 min. Quenched the reaction with saturated aqueous Rochelle's salt (50 mL) and the volatiles were removed in vacuo. The aqueous residue was extracted with ether (3 x 50 mL). The ether was combined and washed with brine (20 mL), dried over Na2SO4 and filtered. The filtrate was evaporated onto silica gel and purified via flash chromatography (0% to 20%; EtOAc in hexanes). MS m/z = 334 [M+Na]+. Calc'd for C19H2iNO3: 311.

Reference： [1]Patent: WO2007/62007,2007,A1 .Location in patent: Page/Page column 159

36
[ 127474-54-8 ]
[ 159635-49-1 ]
[ 1001647-37-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	[1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In dichloromethane; at 40℃; for 12h;	Anhydrous dichloromethane (4 mL, 0.2 M) is added via syringe to 10-B (193 mg, 0.766 mmol, 1.0 eq.), and Hoveyda-Grubbs 2nd Generation metathesis catalyst (l,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene) dichloro (o- isopropoxyphenylmethylene) ruthenium II dichloride) (98 mg, 0.115 mmol, 15 mol %) under a nitrogen atmosphere. N-Boc-4-methylenepiperidine (604 mg, 3.06 mmol, 4.0 eq.) is added via syringe and the reaction is fitted with a reflux condenser and heated to 40 0C for 12 hours. After the reaction is complete as shown by LC/MS, the reaction mixture is directly purified by automated silica-gel purification (0-100% ethyl acetate in hexanes) to provide Reference Compound 10 as a dark green oil. MS m/z 422.3 (M-Boc + 1).

Reference： [1]Patent: WO2008/97673,2008,A1 .Location in patent: Page/Page column 29-30

37
CF₃O₃S^(1-)*C₃₁H₃₅N₂O₂S⁽¹⁺⁾ [ No CAS ]
[ 127474-54-8 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 4105 - 4108

38
[ 1271811-51-8 ]
[ 127474-54-8 ]
[ 1271811-54-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 48h;	To a mixture of (R)-2-benzyloxycarbonylamino-pent-4-enoic acid 39.3 (2.75 g, 1 1.0 mmol), HATU (4.2 g, 1 1.02 mmol), HOBt (1.5 g, 1 1.0 mmol) and DIEA (5.7 mL, 33.1 mmol) in DMF (20 mL) was was added (R)-£e/ -butyl 3-(allylamino)piperidine-l- carboxylate 39.2 (2.7 g, 1 1.0 mmol) at rt. The mixture was stirred for 48 h at rt, diluted with a ice cold brine (400 mL) solution to precipitate the product. The precipitated dissolved in EtOAc and washed with sodium bicarbonate. The organics were dried(MgSC^), filtered and concentrated in vacuo to afford a solid which purified by flash chromatography (gradient hexanes/ EtOAc, 0%-40%) to afford 3.5 l g, 64%. LCMS, m z= 372 [M - tBuC02]+

Reference： [1]Patent: WO2011/29046,2011,A1 .Location in patent: Page/Page column 213

39
[ 1069-48-3 ]
[ 16338-48-0 ]
[ 127474-54-8 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2012,vol. 84,p. 22 - 26

40
[ 501-53-1 ]
[ 127474-54-8 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2012,vol. 84,p. 22 - 26

41
[ 133773-64-5 ]
[ 16338-48-0 ]
[ 127474-54-8 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2012,vol. 84,p. 22 - 26

42
[ 127474-54-8 ]
[ 475504-31-5 ]

Reference： [1]Organic Process Research and Development,2002,vol. 6,p. 762 - 766

43
[ 127474-54-8 ]
[ 475504-32-6 ]
[ 475504-31-5 ]

Reference： [1]Organic Process Research and Development,2002,vol. 6,p. 762 - 766

44
[ 127474-54-8 ]
[ 321744-26-7 ]

Reference： [1]Organic Process Research and Development,2002,vol. 6,p. 762 - 766
[2]Organic Process Research and Development,2002,vol. 6,p. 762 - 766

45
[ 50299-14-4 ]
[ 501-53-1 ]
[ 127474-54-8 ]

Reference： [1]Organic Process Research and Development,2002,vol. 6,p. 762 - 766

46
[ 127474-54-8 ]
(2S,6R)-6-amino-2-((tertbutoxycarbonyl)amino)-7-oxo-7-(tritylamino)heptanoic acid [ No CAS ]