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Merck
CN

ALD00618

(+)-PI Reagent

≥95%

Synonym(s):

(2S,3aR,5S,7aR)-7a-methyl-2-((perfluorophenyl)thio)-5-(prop-1-en-2-yl)hexahydrobenzo[d][1,3,2]oxathiaphosphole 2-sulfide, Phosphorus Incorporation reagent

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About This Item

Empirical Formula (Hill Notation):
C16H16F5OPS3
CAS Number:
2269472-43-5
Molecular Weight:
446.46
MDL number:
MFCD34470702
UNSPSC Code:
12352005
NACRES:
NA.22

Key Documents

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Product Name

(+)-PI Reagent, ≥95%

InChI key

CZCFCQOKUBIPHN-DWBMIXFYSA-N

InChI

1S/C16H16F5OPS3/c1-7(2)8-4-5-16(3)9(6-8)25-23(24,22-16)26-15-13(20)11(18)10(17)12(19)14(15)21/h8-9H,1,4-6H2,2-3H3/t8-,9+,16+,23?/m0/s1

SMILES string

Fc1c(c(c(c(c1F)F)S[P]2(=S)S[C@H]3[C@](O2)(CC[C@@H](C3)C(=C)C)C)F)F

assay

≥95%

form

crystals

mp

119-124 °C

Quality Level

100

Application

(+)-PI Reagent is an air- and moisture-tolerant, reagent developed in the Baran lab for stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides. The enantiomer, (−)-PI Reagent, is also available.

Learn more about PI and PSI reagents

Other Notes

Enantiodivergent formation of C-P bonds: synthesis of P-chiral phosphines and methyl-phosphonate oligonucleotides

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP8973

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Dongmin Xu et al.
Journal of the American Chemical Society, 142(12), 5785-5792 (2020-02-29)
Phosphorus Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct

Articles

PI and PSI – Chiral phosphorus incorporation harnessing the potential of P(V)

PI and PSI reagents are a platform of phosphate-based reagents for phosphorylation and phosphothiolation of nucleotides and peptides developed by the Baran lab.

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