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ALD00633

Sigma-Aldrich

Methyl (+)-PI Reagent

≥95%

Synonym(s):

1,3,2-Benzoxathiaphosphole, hexahydro-2,7a-dimethyl-5-(1-methylethenyl)-, 2-sulfide, (2R,3aR,5S,7aR)

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About This Item

Empirical Formula (Hill Notation):
C11H19OPS2
CAS Number:
2408772-80-3
Molecular Weight:
262.37
UNSPSC Code:
12352005
NACRES:
NA.06

Quality Level

100

Assay

≥95%

form

powder

storage temp.

2-8°C

SMILES string

C[C@]1(O[P@](S2)(C)=S)[C@@]2([H])C[C@@H](C(C)=C)CC1

Application

Methyl (+)-PI Reagent is a methyl substituted analog of the air and moisture-tolerant (+-)-PI reagent developed in the Baran lab for stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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