| Identification | More | [Name]
N-BOC-O-Benzyl-L-serine | [CAS]
23680-31-1 | [Synonyms]
Boc-Hser(Bzl)-OH
BOC-L-SER(TBU)-OH
BOC-O-T-BUTYL-L-SERINE
BOC-O-TERT-BUTYL-L-SERINE
BOC-SER(BU)-OH
BOC-SER(BUT)-OH
BOC-SERINE(TBU)-OH
BOC-SER-OTBU
BOC-SER(TBU)-OH
N-ALPHA-T-BUTOXYCARBONYL-O-T-BUTYL-L-SERINE
N-ALPHA-TERT-BUTYLOXYCARBONYL-O-TERT-BUTYL-L-SERINE
N-Boc-D-Serine(Benzyl Ether)
n-[(1,1-dimethylethoxy)carbonyl]-o-(phenylmethyl)-l-serin
N-T-BOC-O-BENZYL-L-SERINE CRYSTALLINE
N-ALPHA-T-BUTYLOXYCARBONYL-O-BENZYL-L-SERINE
NALPHA-tert-Butoxycarbonyl-O-benzyl-L-serine
N-(tert-Butoxycarbonyl)-O-benzyl-L-serine
N-[(1,1-Dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine
N-BOC-O-Benzyl-L-serine
BOC-O-BENZYL-L-SER-OH | [EINECS(EC#)]
245-820-1 | [Molecular Formula]
C15H21NO5 | [MDL Number]
MFCD00079666 | [Molecular Weight]
295.33 | [MOL File]
23680-31-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [Melting point ]
58-60 °C(lit.)
| [alpha ]
21.5 º (c=2, ethanol) | [Boiling point ]
437.02°C (rough estimate) | [density ]
1.1454 (rough estimate) | [refractive index ]
22 ° (C=2, EtOH) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Solid | [pka]
3.53±0.10(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]20/D +20±1°, c = 2% in ethanol: water (4:1) | [BRN ]
3064461 | [Major Application]
peptide synthesis | [InChI]
1S/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)10-20-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/t12-/m0/s1 | [InChIKey]
DMBKPDOAQVGTST-LBPRGKRZSA-N | [SMILES]
CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)C(O)=O | [CAS DataBase Reference]
23680-31-1(CAS DataBase Reference) | [EPA Substance Registry System]
23680-31-1(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362 | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29242990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
N-Boc-O-benzyl-L-serine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
Example 36 Synthesis of N-tert-butoxycarbonyl-O-benzyl-L-serine 39: Boc-L-serine (15 g, 73.09 mmol) was dissolved in DMF (300 mL) at 0 °C, NaH (6.43 g, 160.80 mmol, 60% mineral oil dispersion) was slowly added, and the reaction temperature was maintained at 0 °C and stirred for 1.5 hours. Subsequently, benzyl bromide (13.75 g, 80.40 mmol) was added, and the reaction mixture was gradually warmed to room temperature and continued to stir overnight. Upon completion of the reaction, DMF was removed by evaporation under reduced pressure and the residue was dissolved in H2O. The crude product was partitioned between water and Et2O. The aqueous phase was acidified with 3N HCl to pH < 4 and then extracted three times with EtOAc. The EtOAc extracts were combined, washed with H2O, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give N-tert-butoxycarbonyl-O-benzyl-L-serine (17.27 g, 80% yield). | [References]
[1] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3225 - 3229
[2] Patent: US2004/121316, 2004, A1
[3] Patent: US2005/239054, 2005, A1
[4] Patent: WO2014/120783, 2014, A1. Location in patent: Paragraph 00145
[5] Patent: WO2018/26763, 2018, A1. Location in patent: Page/Page column 81 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|