Short synthesis of tert-butyl-hydroxylated 3,5-di-tert-butyl-4-hydroxybenzaldehyde:: Synthesis of tert-butyl-hydroxylated S-2474

被引：17

作者：

Inagaki, M ^{[1
]}

Matsumoto, S ^{[1
]}

Tsuri, T ^{[1
]}

机构：

[1] Shionogi & Co Ltd, Discovery Res Labs, Fukushima Ku, Osaka 5530002, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 03期

关键词：

D O I：

10.1021/jo020587v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a very short synthesis of tertbutyl-hydroxylated di-tert-butyl-4-hydroxybenzaldehyde in which the HBr-DMSO system is used as an effective oxidant (overall yield of 45% for the entire four-step process from 2-tert-butyl-p-cresol). We also accomplished the synthesis of a major metabolite of the antiarthritic drug candidate S-2474.

引用

页码：1128 / 1131

页数：4

共 27 条

[1] METABOLIC-ACTIVATION OF BUTYLATED HYDROXYTOLUENE BY MOUSE BRONCHIOLAR CLARA CELLS [J].

BOLTON, JL ;

THOMPSON, JA ;

ALLENTOFF, AJ ;

MILEY, FB ;

MALKINSON, AM .

TOXICOLOGY AND APPLIED PHARMACOLOGY, 1993, 123 (01) :43-49

[2]

BOLTON JL, 1991, DRUG METAB DISPOS, V19, P467

[3] FORMATION AND REACTIVITY OF ALTERNATIVE QUINONE METHIDES FROM BUTYLATED HYDROXYTOLUENE - POSSIBLE EXPLANATION FOR SPECIES-SPECIFIC PNEUMOTOXICITY [J].

BOLTON, JL ;

SEVESTRE, H ;

IBE, BO ;

THOMPSON, JA .

CHEMICAL RESEARCH IN TOXICOLOGY, 1990, 3 (01) :65-70

[4] THE ENZYMATIC FORMATION AND CHEMICAL-REACTIVITY OF QUINONE METHIDES CORRELATE WITH ALKYLPHENOL-INDUCED TOXICITY IN RAT HEPATOCYTES [J].

BOLTON, JL ;

VALERIO, LG ;

THOMPSON, JA .

CHEMICAL RESEARCH IN TOXICOLOGY, 1992, 5 (06) :816-822

[5]

CHOW YL, 1982, SYNTHESIS-STUTTGART, P648

[6] Selective induction of apoptosis in mouse and human lung epithelial cell lines by the tert-butyl hydroxylated metabolite of butylated hydroxytoluene:: a proposed role in tumor promotion [J].

Dwyer-Nield, L ;

Thompson, JA ;

Peljak, G ;

Squier, MKT ;

Barker, TD ;

Parkinson, A ;

Cohen, JJ ;

Dinsdale, D ;

Malkinson, AM .

TOXICOLOGY, 1998, 130 (2-3) :115-127

[7] N-MONOALKYLATION AND ARYL BROMINATION OF CERTAIN AMINES WITH ETHYL BROMIDE IN DIMETHYL SULFOXIDE [J].

FLETCHER, TL ;

PAN, HL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (18) :4812-4812

[8] THE OXIDATION OF ACETOPHENONES TO ARYLGLYOXALS WITH AQUEOUS HYDROBROMIC ACID IN DIMETHYLSULFOXIDE [J].

FLOYD, MB ;

DU, MT ;

FABIO, PF ;

JACOB, LA ;

JOHNSON, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5022-5027

[9]

GOTO K, 1990, Patent No. 9985

[10] DOWN-REGULATION BY BUTYLATED HYDROXYTOLUENE OF THE NUMBER AND FUNCTION OF GAP-JUNCTIONS IN EPITHELIAL-CELL LINES DERIVED FROM MOUSE LUNG AND RAT-LIVER [J].

GUAN, X ;

HARDENBROOK, J ;

FERNSTROM, MJ ;

CHAUDHURI, R ;

MALKINSON, AM ;

RUCH, RJ .

CARCINOGENESIS, 1995, 16 (10) :2575-2582

← 1 2 3 →