123639-56-5|L-N-Benzylserine Methyl Ester| Ambeed

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Quality Control of [ 123639-56-5 ] Purity: 98% SDS Specification

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Product Details of [ 123639-56-5 ]

CAS No. :	123639-56-5
Formula :	C₁₁H₁₅NO₃
M.W :	209.24
SMILES Code :	O=C(OC)[C@@H](NCC1=CC=CC=C1)CO
MDL No. :	MFCD07367716
InChI Key :	GMZGWPPEZCREPP-JTQLQIEISA-N
Pubchem ID :	11790456

Safety of [ 123639-56-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 123639-56-5 ]

* 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.

Downstream synthetic route of [ 123639-56-5 ]

[ 123639-56-5 ] Synthesis Path-Downstream 1~35

1
[ 40216-75-9 ]
[ 123639-56-5 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 4917 - 4920.
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6279 - 6286.
[3]Tetrahedron Letters,2001,vol. 42,p. 2019 - 2021.
[4]Journal of Organic Chemistry,2011,vol. 76,p. 5703 - 5708.
[5]Journal of the American Chemical Society,2012,vol. 134,p. 5072 - 5075.

2
[ 5874-57-7 ]
[ 100-52-7 ]
[ 123639-56-5 ]

Yield	Reaction Conditions	Operation in experiment
60%		TEA (44.8 ml, 321.38 mmol) was added to a solution of methyl D-serinate hydrochloride (50 g, 321.38 mmol) and benzaldehyde (33 ml, 321.38 mmol) in methanol (250 ml) at 0C. The resulting suspension was stirred at room temperature for 2 hours. Then sodium borohydride (24 g, 634.39 mmol) was added slowly and the mixture stirred at room temperature for another 2 hours. The reaction mixture was quenched with water (200 ml), extracted with DCM (3 x 100 ml), the organic layer was dried over sodium sulphate, filtered and evaporated. The crude product was purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford methyl N-benzyl-D-serinate (40 g, 60%) as a colourless oil. 1H NMR (400 MHz, CDCIs, 30C) 2.51 (2H, s), 3.48 (1H, dd), 3.65 (1H, dd), 3.76 - 3.84 (5H, m), 3.92 (1H, d), 7.36 (5H, m). m/z: ES+ [M+H]+ = 210.
		The title compound was prepared according to literature (ref. JOC, 1990, 55(1 ), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 00C under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCI (20% solution) at 00C and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3 x 50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95g). m/z = 210 [M+H]+
		To (2R)-3-hydroxy-1-methoxy-1-oxopropan-2-aminium chloride (1 eq.) in MeOH (1.3 M) at 0C was added triethylamine (1 eq.). The reaction mixture was stirred for 10 minutes and benzaldehyde (1 eq) was added. The reaction mixture was stirred for 2 hours and NaBH4(1.5 eq.) was added portionwise to the reaction mixture over 30 mm. The reaction mixture was stirred at rt for 5hours and poured into a 1:1 mixture of saturated aqueous NH4C1 and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and water, dried over Na2504, filtered and concentrated. The crude product was used as such for the next step.

References: [1]Organic Letters,2007,vol. 9,p. 3825 - 3828.
[2]ARKIVOC,2010,vol. 2010,p. 108 - 126.
[3]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.
[4]Patent: WO2019/215203,2019,A1 .Location in patent: Page/Page column 36; 41-42.
[5]Journal of Organic Chemistry,1992,vol. 57,p. 4470 - 4477.
[6]Tetrahedron Letters,2001,vol. 42,p. 7893 - 7897.
[7]Patent: WO2007/28654,2007,A1 .Location in patent: Page/Page column 94-95.
[8]Patent: WO2015/95265,2015,A1 .Location in patent: Page/Page column 24.

3
[ 123639-56-5 ]
[ 77-76-9 ]
[ 131110-77-5 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 4917 - 4920.
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6279 - 6286.

4
[ 123639-56-5 ]
[ 501-53-1 ]
N-benzyl-N-carbobenzyloxy-D-serine methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 8275 - 8278.
[2]Tetrahedron Letters,2001,vol. 42,p. 2019 - 2021.

5
[ 123639-56-5 ]
[ 630-19-3 ]
(2R,4R)-3-Benzyl-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester [ No CAS ]
(2S,4R)-3-Benzyl-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 7893 - 7897.

6
[ 123639-56-5 ]
[ 18162-48-6 ]
[ 794518-57-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 16h;	To <strong>[123639-56-5]methyl N-benzyl-D-serinate</strong> (1 eq.) in CH2C12 (0.3 M) at rt were added triethylamine (1 eq) and DMAP (0.05 eq). The reaction mixture was cooled to 0C and TBS-Cl (1.1 eq) was added. The reaction mixture was stirred at rt for 1 6hrs, water was added and theaqueous layer was extracted with CH2C12. The combined organic layers were washed with saturated aqueous NH4C1, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step.

References: [1]Organic Letters,2007,vol. 9,p. 3825 - 3828.
[2]European Journal of Organic Chemistry,2005,p. 1427 - 1443.
[3]Organic Letters,2004,vol. 6,p. 3743 - 3746.
[4]Patent: WO2015/95265,2015,A1 .Location in patent: Page/Page column 24; 25.

7
[ 24424-99-5 ]
[ 123639-56-5 ]
[ 887128-07-6 ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.
[2]ARKIVOC,2010,vol. 2010,p. 108 - 126.

8
[ 123639-56-5 ]
[ 58479-61-1 ]
[ 852946-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 0℃;	To methyl (2R>-34iydroxy-.2--[benzyiaminojpropanoate (500g, 2.39 mol) in 2 L CH2C12were added NEt3 (290g. 187 mol) and cat. DMAP (15g. 0A2 mol). Cooled to 0C and TBDPS- Ci (690g, 2.51 mol) was added dropwise. Water (3 L) and CH2C12 (3 L) were added, layers wereseparated, combined organic layers were washed with sat NH4CI, dried over Na2SO4 and concentrated to give methyl (2R)-3-(22-dimethyl- 1,1 -diphenyl-- 1 -silapropoxy)-2- [henzyiarnino]propanoate, which was used as such for the next step without any further purification.

References: [1]European Journal of Organic Chemistry,2005,p. 1427 - 1443.
[2]Patent: WO2016/106628,2016,A1 .Location in patent: Page/Page column 94.

9
[ 123639-56-5 ]
C₂₂H₃₆ClNO₃Si [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 3825 - 3828.

10
[ 123639-56-5 ]
C₂₁H₃₆ClNO₂Si [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 3825 - 3828.

11
[ 123639-56-5 ]
benzyl-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.
[2]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.

12
[ 123639-56-5 ]
[ 887128-13-4 ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.

13
[ 123639-56-5 ]
[ 887128-09-8 ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.

14
[ 123639-56-5 ]
[ 887128-08-7 ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.

15
[ 123639-56-5 ]
[ 852946-11-3 ]

References: [1]European Journal of Organic Chemistry,2005,p. 1427 - 1443.
[2]Patent: WO2016/106628,2016,A1 .

16
[ 123639-56-5 ]
[ 887128-12-3 ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.

17
[ 123639-56-5 ]
[ 887128-11-2 ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.

18
[ 123639-56-5 ]
ethyl (2E,4S)-4-{benzyl[(2E)-4-hydroxy-3-methyl-2-butenyl]amino}-5-[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate [ No CAS ]

References: [1]European Journal of Organic Chemistry,2005,p. 1427 - 1443.

19
[ 123639-56-5 ]
[ 852946-12-4 ]

References: [1]European Journal of Organic Chemistry,2005,p. 1427 - 1443.

20
[ 123639-56-5 ]
[ 852946-13-5 ]

References: [1]European Journal of Organic Chemistry,2005,p. 1427 - 1443.

21
[ 123639-56-5 ]
[ 134930-26-0 ]

References: [1]Heterocyclic Communications,2005,vol. 11,p. 343 - 346.
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6279 - 6286.
[3]Tetrahedron Letters,1990,vol. 31,p. 4917 - 4920.

22
[ 123639-56-5 ]
[ 794518-59-5 ]

References: [1]European Journal of Organic Chemistry,2005,p. 1427 - 1443.
[2]Organic Letters,2004,vol. 6,p. 3743 - 3746.
[3]Patent: WO2015/95265,2015,A1 .

23
[ 123639-56-5 ]
[ 794518-65-3 ]