ALD00602

(–)-PSI Reagent

95%

• Synonym(s): (2S,3aS,6R,7aS)-3a-Methyl-2-((perfluorophenyl)thio)-6-(prop-1-en-2-yl)hexahydrobenzo[d][1,3,2]oxathiaphosphole 2-sulfide, (–)-Ψ, Phosphorus-Sulfur Incorporation Reagent
• Empirical Formula (Hill Notation): C₁₆H₁₆F₅OPS₃
• CAS Number: 2245335-70-8
• Molecular Weight: 446.46
• MDL number: MFCD32068365
• UNSPSC Code: 12352101
• NACRES: NA.22

Properties

• assay: 95%
• form: powder or crystals
• mp: 103-107 °C
• SMILES string: Fc1c(c(c(c(c1F)F)S[P]2(=S)S[C@@]3([C@@H](O2)C[C@@H](CC3)C(=C)C)C)F)F
• 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
• InChI key: YPYCUYPOHPPYAS-QSHUGKRNSA-N

Description

Application

Air- and moisture-tolerant, this (-)-PSI Reagent was developed in the Baran lab for stereocontrolled synthesis of phosphorothioate oligonucleotides. The enantiomer, (+)-PSI Reagent, is also available (cat# ALD00604).
The PSI Reagents open access to thiophosphate-based nucleotide molecules with therapeutic promise as demonstrated by the Baran lab in the preparation of pure stereoisomers of cyclic dinucleotides (CDNs) and antisense oligonucleotides (ASOs).

Learn more about PI and PSI reagents

Other Notes

Unlocking P(V): Reagents for chiral phosphorothioate synthesis

PSI on OpenFlask

Legal Information

PCT/US2019/027256; U.S. Nonprovisional Patent Application #16/382,692

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable