PyBOP

PyBOP
Names


IUPAC name (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate
Other names PyBOP
Identifiers
CAS Number	128625-52-5^N
3D model (JSmol)	Interactive image
ChemSpider	2006820^Y
ECHA InfoCard	100.125.168
PubChem CID	2724699
InChI InChI=1S/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1^Y Key: VIAFLMPQBHAMLI-UHFFFAOYSA-N^Y InChI=1/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1 Key: VIAFLMPQBHAMLI-UHFFFAOYAY
SMILES F[P-](F)(F)(F)(F)F.n4nn(O[P+](N1CCCC1)(N2CCCC2)N3CCCC3)c5ccccc45
Properties
Chemical formula	C₁₈H₂₈F₆N₆OP₂
Molar mass	520.40 g·mol⁻¹
Appearance	White crystals
Melting point	150 °C (302 °F; 423 K)
Hazards
Main hazards	Irritant
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26-S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

PyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) is a peptide coupling reagent used in solid phase peptide synthesis. It is used as a substitute for the BOP reagent, thus avoiding the formation of the carcinogenic side product HMPA.^[1]

It has also been used for condensation of d-LA into d-LSD.^[2]

References

↑ Coste, J.; Le-Nguyen, D.; Castro, B. (1990). "PyBOP®: A new peptide coupling reagent devoid of toxic by-product". Tetrahedron Letters. 31 (2): 205. doi:10.1016/S0040-4039(00)94371-5.
↑ Hardison, Casey William (2005). "Novel Condensation of D-LA into D-LSD via PyPOB [sic]". The Entheogen Review. XIV (1): 94.

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PyBOP

See also

References