(2S,3S)-2-nitro-5-phenyl-1,3-pentanediol

 (2S,3S)-2-nitro-5-phenyl-1,3-pentanediol are as follows:

 [α]_D ²⁴ −17.7° (c 0.86, chloroform, 98% ee), 

mp 101-102°C; 

¹H NMR δ: 1.83-1.95 (m, 2 H), 2.19 (br-t, 1 H, J = 6.2), 2.44 (br-d, 1 H, J = 7.5), 2.75 (m, 1 H), 2.90 (m, 1 H), 4.03-4.23 (m, 3 H), 4.57 (ddd, 1 H, J = 4.0, 5.2, 6.7), 7.17-7.35 (m, 5 H) ; 

13C NMR δ: 31.45 (CH), 35.15 (CH₂), 61.78 (CH₂), 69.53 (CH₂), 92.08 (CH), 126.33 (CH), 128.43 (CH), 128.64 (CH) 140.56 (C) ; 

IR (KBr) cm⁻¹: 3332, 1559, 1369 ; 

FABMS (glycerol) m/z 226 (M⁺+1), 161, 91 (base peak). 

Anal. calcd for C₁₁H₁₅NO₄: C, 58.66; H, 6.71; N, 6.22. Found: C, 58.47; H, 6.77; N, 5.93.

http://orgsyn.org/demo.aspx?prep=v78p0014

http://onlinelibrary.wiley.com/doi/10.1002/0471264180.os078.02/abstract