HATU

한글명:HATU

카스 번호148893-10-1

상품명:HATU

CBNumberCB0122630

분자식C10H15F6N6OP

포뮬러 무게380.24

MOL 파일148893-10-1.mol

화학적 성질

녹는점	183-188 °C (dec.)
RTECS 번호	XZ5633000
저장 조건	2-8°C
용해도	>16mg/mL in DMSO
물리적 상태	powder to crystaline
색상	흰색에서 거의 흰색
수용성	아세토니트릴에 용해됩니다. 물에 불용성.
InChI	InChI=1S/C10H15N6O.F6P/c1-13(2)10(14(3)4)15-8-6-5-7-11-9(8)16(17)12-15;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
InChIKey	KZAWCZZRROLLDL-UHFFFAOYSA-N
SMILES	[P+5]([F-])([F-])([F-])([F-])([F-])[F-].C(=[N+]1/N=N(=O)C2=NC=CC=C/12)(\N(C)C)/N(C)C
CAS 데이터베이스	148893-10-1(CAS DataBase Reference)
EPA	1H-1,2,3-Triazolo[4,5-b]pyridinium, 1-[bis(dimethylamino)methylene]-, hexafluorophosphate(1-), 3-oxide (148893-10-1)

위험 및 안전 성명

위험품 표기

Xi,Xn,E

위험 카페고리 넘버

36/37/38-20/21/22-2

안전지침서

26-37/39-36/37-36-35

유엔번호(UN No.)

1325

WGK 독일

F 고인화성물질

10-21

위험 등급

4.1

포장분류

Ⅱ

HS 번호

29339999

NFPA 704:

	2
2		0

그림문자(GHS)

HATU 화학적 특성, 용도, 생산

개요
HATU, first prepared by Louis A. Carpino in 1993, is widely used in carboxylic acid amidation reactions. It acts as a facilitator of amide bond generation by activating the carboxyl group.
화학적 성질
White crystalline to off-white powder
용도
HATU[148893-10-1] is a coupling reagent and used as an additive in peptide synthesis. It is also involved efficiently to speed up the coupling process and reduces the loss of chiral integrity.
Reagent for: Synthesis of Aurora A kinase inhibitors, HPLC assay to determine D- and L- acid enantiomers in human plasma, Amide bond formation reactions.
Catalyst for: Selective acylation, Selecocyclization-oxidation deselenation sequence.
화학 반응
HATU is a very promising coupling agent for chemical protein synthesis.

This strategy was exploited to prepare macrocycles from the trimeric linear arylopeptoids (ortho-, meta-, and para-) containing isopropyl or ethyl side chains, synthesized as described by Hjelmgaard et al. The cyclization procedure reported for α,β-cyclopeptoids was applied. The linear arylopeptoids were cyclized in the presence of HATU and DIPEA in CH?Cl?/DMF (4:1) after the deprotection of the tert-butyl group in TFA/CH?Cl?.

After the synthesis of the Fmoc-protected monomers, the oligomers were synthesized on the 2-chlorotrityl resin with excellent yield of coupling (>98%). The trimers and tetramers of the different isomers were synthesized in good overall yield (60-84%). Then, the crude oligomers were cyclized in DMF in the presence of HATU and DIPEA in high dilution (3 × 10?3 M) to furnish the cyclized trimers and tetramers in good yields ranging between 32% and 72%.
Synthesis
The synthesis of HATU is as follows:The resulting residue treated with 2-Methoxycarbonylamino-3-methyl-butyric acid (60 mg, 0.343 mmol) and HATU (130 mg, 0.343 mmol), suspended in DMF (3 mL) and cooled to 0° C. DIPEA (0.272 mL, 1.56 mmol) was added dropwise. After stirring for 4 h, NaOH (5M in H2O, 0.300 mL, 1.5 mmol) was added. This mixture was stirred for 3 h then diluted with EtOAc and washed with 1 M LiOH (2*) then brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude residue was then purified by HPLC to afford the title compound (53 mg, 44%).
참고 문헌
[1] CHAWLA P A, SHOME A, JHA K T. Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium (HATU): A Unique Cross-Coupling Reagent[J]. SynOpen, 2023, 66 2: 0. DOI:10.1055/s-0042-1751499.
[2] LOUIS A. CARPINO. Comparison of the Effects of 5- and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers?,?[J]. Organic Letters, 2000, 2 15: 2253-2256. DOI:10.1021/ol006013z.

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