SCOPUS 정보 검색 플랫폼

Volumn 43, Issue 27, 2002, Pages 4793-4796

Solid-phase synthesis of PhTX-3.2.4 and PhTX-2.3.3 derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALDEHYDE DERIVATIVE; BENZHYDRYL DERIVATIVE; CARBAMIC ACID DERIVATIVE; CHLORIDE; DIAMINE DERIVATIVE; PHILANTHOTOXIN; POLYAMINE;

ARTICLE; CHEMICAL STRUCTURE; METHODOLOGY; PROTECTION; REDUCTION; SYNTHESIS;

EID: 0036644232 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(02)00928-0 Document Type: Article

Times cited : (20)

References (31)

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2
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- and references cited therein
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11
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- Moya, E.¹ Blagbrough, I.S.²

19
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- (2000) Tetrahedron Lett. , vol.41 , pp. 6149-6152
- Hone, N.D.¹ Payne, L.J.²

21
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- Wang, F.¹ Manku, S.² Hall, D.G.³

22
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- (2002) Tetrahedron Lett. , vol.43 , pp. 3125-3128
- Jönsson, D.¹ Undén, A.²

23
- 0009513490
- 4 (0.9 g, 23.6 mmol, 0.5 equiv.) was added slowly and the reduction was left to stir overnight. TLC (petroleum ether/EtOAc, 9/1) indicated completeness of the reduction and the mixture was poured onto water (250 ml), stirred for 1 h and 4-methoxy benzhydrol could be filtered off and dried. 4-Methoxy benzhydrol (5 g, 23.3 mmol) was dissolved in dried DCM (50 ml), oxalyl chloride (2.25 ml, 25.7 mmol, 1.1 equiv.) was added dropwise and the reaction was left stirring for 2 h at room temperature. The solvent was evaporated and 4-methoxydityl chloride was crystallized and recrystallized from warm petroleum ether. Yield: 5.4 g, 99%.

24
- 0009513491
- 4,4′-Dimethoxy dityl chloride (Dod-Cl): 4,4′-dimethoxy benzhydrol (6.0 g, 24.6 mmol) was dissolved in dried DCM (60 ml), oxalyl chloride (2.36 ml, 27 mmol, 1.1 equiv.) was added dropwise and the reaction was left with stirring for 1.5 h at room temperature. The solvent was evaporated and the 4,4′-dimethoxydityl chloride was crystallized and recrystallized from warm petroleum ether. Yield: 5.8 g, 90%.

28
- 0009502642
- 2O and solvent B was 0.1% TFA/acetonitrile. Detection was performed at 279 nm, and the purity was measured by integration of the absorbance of the Fmoc group of intermediate products or the tyrosine of the final products.

29
- 0009476714
- MALDI-TOF analyses were performed on a Voyager-DE STR (Applied Biosystems, USA) in reflector mode with α-cyano-hydroxy cinnamic acid (Fluka) as matrix. Internal calibration was made against the resolved matrix peak at 379.0930 and all obtained molecular weights are monoisotopic.

30
- 0009543035
- Overall yields are the isolated yield compared to the theoretical maximum yield on initial resin loading (0.6 mmol/g).

31
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- (1978) J. Org. Chem. , vol.43 , pp. 2480-2482
- Mancuso, A.¹ Huang, S.² Swern, D.³

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