| Identification | More | [Name]
Boc-L-serine methyl ester | [CAS]
2766-43-0 | [Synonyms]
BOC-L-SERINE METHYL ESTER
BOC-SERINE-OME
BOC-SER-OME
N-ALPHA-T-BUTOXYCARBONYL-L-SERINE METHYL ESTER
N-BOC-L-SERINE METHYL ESTER
N-(TERT-BUTOXYCARBONYL)-L-SERINE METHYL ESTER
Butoxycarbonylserinemethylester
N-T-BOC-L-SERINE METHYL ESTER
BOC-SER-OME, BOC-L-SERINE METHYL ESTER
Boc-L-Ser-OMe (oil)
N-alpha-t-Butyloxycarbonyl-L-serine methyl ester (oil)
BOC-L-SERINE METHYLESTER OIL
Boc-L-serine methyl ester, N-(tert-Butoxycarbonyl)-L-serine methyl ester | [EINECS(EC#)]
690-499-7 | [Molecular Formula]
C9H17NO5 | [MDL Number]
MFCD00191869 | [Molecular Weight]
219.23 | [MOL File]
2766-43-0.mol |
| Chemical Properties | Back Directory | [alpha ]
-18 º (c=5 in methanol) | [Boiling point ]
354.3±32.0 °C(Predicted) | [density ]
1.082 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.452(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
-15°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Liquid or Oil | [pka]
10.70±0.46(Predicted) | [color ]
Colorless to yellow | [Optical Rotation]
[α]20/D 18°, c = 5 in methanol | [Water Solubility ]
Slightly soluble in water. | [BRN ]
3545389 | [Major Application]
peptide synthesis | [InChI]
1S/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-11)7(12)14-4/h6,11H,5H2,1-4H3,(H,10,13)/t6-/m0/s1 | [InChIKey]
SANNKFASHWONFD-LURJTMIESA-N | [SMILES]
COC(=O)[C@H](CO)NC(=O)OC(C)(C)C | [CAS DataBase Reference]
2766-43-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P280-P304+P340-P305+P351+P338 | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29241990 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [Chemical Properties]
Liquid | [Uses]
Boc-L-serine methyl ester is a derivative of L-Serine Methyl Ester Hydrochloride (S271005) derivative. Boc-L-serine methyl ester is an amino acid derivative used in the preparation of Tn antigen, L-glutamic acid p-nitroanilide analogs and new biomedical polymers having Serine and Threonine side groups.
| [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
General procedure for the synthesis of Boc-L-serine methyl ester from di-tert-butyl dicarbonate and L-serine methyl ester hydrochloride: crude L-serine methyl ester hydrochloride (0.29 mol) was suspended in dichloromethane (200 mL), followed by the addition of triethylamine (79 mL, 0.57 mol) and di-tert-butyl dicarbonate (68 g, 0.31 mol) to the mixture. The reaction was carried out at 0°C. After removal of the cooling bath, the reaction mixture was stirred at room temperature overnight and then diluted with methyl tert-butyl ether (300 mL). The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by fast column chromatography on silica gel to afford Boc-L-serine methyl ester (60 g, 94% yield) as a colorless oil. | [References]
[1] European Journal of Organic Chemistry, 2000, # 1, p. 115 - 124
[2] Organic Letters, 2003, vol. 5, # 24, p. 4599 - 4602
[3] Journal of Organic Chemistry, 2015, vol. 80, # 1, p. 40 - 51
[4] Journal of the American Chemical Society, 2016, vol. 138, # 43, p. 14218 - 14221
[5] Organic and Biomolecular Chemistry, 2013, vol. 11, # 19, p. 3089 - 3093 |
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