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Merck
CN

ALD00632

Methyl (-)-PI Reagent

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H19OPS2
CAS Number:
2408772-79-0
Molecular Weight:
262.37
UNSPSC Code:
12352005
NACRES:
NA.06

Key Documents

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Quality Level

100

Assay

≥95%

form

powder

storage temp.

2-8°C

SMILES string

[H][C@@]1(S[P@](O2)(C)=S)[C@]2(C)CC[C@@H](C(C)=C)C1

InChI

1S/C11H19OPS2/c1-8(2)9-5-6-11(3)10(7-9)15-13(4,14)12-11/h9-10H,1,5-7H2,2-4H3/t9-,10+,11+,13?/m1/s1

InChI key

VBFDELVILGOWRT-UCHDHUMISA-N

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000188133
0000188133
0000164248
0000164248

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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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