N-Boc-(S)-2-amino-3-benzyloxy-1-propanol Chemical Properties

Melting point:

66-69 °C(lit.)

alpha 

-14 º (c=1 in chloroform)

Boiling point:

443.1±40.0 °C(Predicted)

Density 

1.105

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

11.58±0.46(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C15H23NO4/c1-15(2,3)20-14(18)16-13(9-17)11-19-10-12-7-5-4-6-8-12/h4-8,13,17H,9-11H2,1-3H3,(H,16,18)/t13-/m0/s1

InChIKey

MSIDLARYVJJEQY-ZDUSSCGKSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@@H](CO)COCC1=CC=CC=C1

CAS DataBase Reference

79069-15-1(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

2924297099

MSDS

• Language:English Provider:SigmaAldrich

N-Boc-(S)-2-amino-3-benzyloxy-1-propanol Usage And Synthesis

Chemical Properties

White to off-white solid

Synthesis

Under an atmosphere of argon, to a solution of 2,5-dioxopyrrolidin-1-yl O-benzyl-N-t-butoxycarbonyl-L-serinate (4.41 g) in tetrahydrofuran(30 mL) was added sodium borohydride (644 mg) in ice bath and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and concentrated to give N-Boc-(S)-2-amino-3-benzyloxy-1-propanol.

References

[1] Synthetic Communications, 1996, vol. 26, # 13, p. 2511 - 2522
[2] Nucleosides and Nucleotides, 1999, vol. 18, # 8, p. 1845 - 1861
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 702 - 713

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