Boc-D-phenylglycinol
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Boc-D-phenylglycinol

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A chiral building block for the synthesis of homochiral N-protected β-amino sulfoxides and α-amino acids.

Category
Amino Alcohol
Catalog number
BAT-000356
CAS number
102089-74-7
Molecular Formula
C13H19NO3
Molecular Weight
237.3
Boc-D-phenylglycinol
IUPAC Name
tert-butyl N-[(1R)-2-hydroxy-1-phenylethyl]carbamate
Synonyms
(R)-2-(Boc-amino)-2-phenylethanol; Boc-D-Phg-ol; (R)-N-(tert-Butoxycarbonyl)-2-phenylglycinol; (R)-tert-butyl (2-hydroxy-1-phenylethyl)carbamate; N-Boc-D-2-phenylglycinol
Appearance
White to off-white powder
Purity
≥ 99 % (HPLC)
Density
1.102 g/cm3
Melting Point
131-137 °C
Boiling Point
382.4 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H19NO3/c1-13(2,3)17-12(16)14-11(9-15)10-7-5-4-6-8-10/h4-8,11,15H,9H2,1-3H3,(H,14,16)/t11-/m0/s1
InChI Key
IBDIOGYTZBKRGI-NSHDSACASA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CO)C1=CC=CC=C1
2. Highly enantio- and diastereoselective Mannich reactions of glycine Schiff bases with in situ generated N-Boc-imines catalyzed by a cinchona alkaloid thiourea
Haile Zhang, Salahuddin Syed, Carlos F Barbas 3rd Org Lett. 2010 Feb 19;12(4):708-11. doi: 10.1021/ol902722y.
Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable alpha-amido sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active alpha,beta-diamino acid derivatives with up to 99% ee and near-perfect diastereoselection.
3. A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric mannich reactions of N-Boc-protected imines
Taichi Kano, Yukako Yamaguchi, Keiji Maruoka Angew Chem Int Ed Engl. 2009;48(10):1838-40. doi: 10.1002/anie.200805628.
The moderate nucleophilicity of the axially chiral amino sulfonamide (S)-1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N-Boc-protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc = tert-butoxycarbonyl, Tf = trifluoromethanesulfonyl).
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