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Merck
CN

ALD00625

PSIO

Synonym(s):

(2S,3aS,6R,7aS)-3a-Methyl-2-((4-bromophenyl)thio)-6-(prop-2-yl)hexahydrobenzo[d][1,3,2]oxathiaphosphole 2-oxide

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About This Item

Empirical Formula (Hill Notation):
C16H22BrO2PS2
CAS Number:
2702251-89-4
Molecular Weight:
421.35
UNSPSC Code:
12141909
NACRES:
NA.22

Key Documents

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storage temp.

2-8°C

Quality Level

100

SMILES string

CC(C)[C@@H]1CC[C@@]2(C)[C@@H](O[P@](S2)(SC3=CC=C(Br)C=C3)=O)C1

InChI

1S/C16H22BrO2PS2/c1-11(2)12-8-9-16(3)15(10-12)19-20(18,22-16)21-14-6-4-13(17)5-7-14/h4-7,11-12,15H,8-10H2,1-3H3/t12-,15+,16+,20?/m1/s1

InChI key

FECFSGBUDPGGDZ-UMXMUBITSA-N

Application

PSIO is a P(V) reagent developed by the Baran Lab as a part of the Ψ platform, used in the direct phosphorylation of alcohols. This reagent is scalable and easy to use under mild conditions, and is functional for a broad substrate scope, including many alcohols that are challenging to otherwise activate.

Learn more about PI and PSI reagents

Other Notes

Mild and Chemoselective Phosphorylation of Alcohols Using a PSI-Reagent

Unlocking P(V):Reagents for chiral phosphorothioate synthesis

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000428355
0000428355
0000155601
0000155567
0000155601

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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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