Abstract
image
[2245335‐71‐9]
C
16
H
16
F
5
OPS
3
(MW 446.4488)
InChI =
1S/C16H16F5OPS3/c1‐7(2)8‐4‐5‐16(3)9(6‐8)22‐23(24,26‐16)25‐15‐13(20)11(18)10(17)12(19)14(15)21/h8‐9H,1,4‐6H2,2‐3H3/t8‐,9?,16+,23‐/m0/s1
InChIKey =
YPYCUYPOHPPYAS‐KUDWSVNUSA‐N
[2245335‐70‐8]
C
16
H
16
F
5
OPS
3
(MW 446.4488) Enantiomer
InChI =
1S/C16H16F5OPS3/c1‐7(2)8‐4‐5‐16(3)9(6‐8)22‐23(24,26‐16)25‐15‐13(20)11(18)10(17)12(19)14(15)21/h8‐9H,1,4‐6H2,2‐3H3/t8‐,9?,16+,23+/m1/s1
InChIKey =
YPYCUYPOHPPYAS‐DPZXBIMTSA‐N
(reagent used for the creation of stereopure thiophosphate bonds
1
)
Alternative Names
: PSI (Phosphorous Sulfur Incorporation), (+)‐PSI or (+)‐Ψ for
2245335‐71‐9
and (−)‐PSI or (−)‐Ψ for
2245335‐70‐8
.
Physical Data
: mp 110 °C; [α]
D
20
= 242 (
c
= 0.5, CH
2
Cl
2
) for 2245335‐71‐9 and [α]
D
20
= −253 (
c
= 0.5, CH
2
Cl
2
) for 2245335‐70‐8.
Solubility
: soluble in acetonitrile, dichloromethane, and tetrahydrofuran. Insoluble in water, methanol, hexanes, and heptane.
Form Supplied in
: white crystals. Stored at ambient conditions. Commercially available.
Analysis of Reagent Purity
: nuclear magnetic resonance spectroscopy.
1,2
31
P (CDCl
3
) = δ 100 ppm. Enantiopurity is best assessed by High‐Performance Liquid Chromatography (HPLC).
1
Preparative Method
: all reagents in the PSI family are derived in a one‐step reaction between a phosphorus salt and an epoxide. The product is crystallized from the reaction mixture, then recrystallized.
1,2
Handling, Storage, and Precautions
: the reagents are stable and can be stored at 0 °C to ambient temperatures. They do not show any hygroscopicity nor aerial oxidation in the solid state. The compounds rapidly decompose in the presence of aqueous base.