NEW APPLICATIONS OF THE PROTECTING GROUP DI-(4-METHOXYPHENYL)METHYL - N-PROTECTION OF URETHANES AND URIDINES, AND EFFICIENT REMOVAL BY EITHER CERIC AMMONIUM-NITRATE SILICA OR 2,3-DICHLORO-5,6-DICYANOQUINONE

被引：6

作者：

ABUSBEIH, K ^{[1
]}

BLEASDALE, C ^{[1
]}

GOLDING, BT ^{[1
]}

KITSON, SL ^{[1
]}

机构：

[1] UNIV NEWCASTLE UPON TYNE,DEPT CHEM,BEDSON BLDG,NEWCASTLE TYNE NE1 7RU,TYNE & WEAR,ENGLAND

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 33期

关键词：

PROTECTION; DEPROTECTION; DI-(4-METHOXYPHENYL)METHYL; URETHANE; URIDINE;

D O I：

10.1016/S0040-4039(00)61291-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The protecting group di-(4-methoxyphenyl)methyl, removable by ceric ammonium nitrate on silica or 2,3-dichloro-5,6-dicyanoquinone, is shown to facilitate syntheses of urethanes (eg vinyl urethane, 1a) and uridine derivatives (eg 2-O-allyluridine, 8).

引用

页码：4807 / 4810

页数：4

共 24 条

[1]

BESSODES M, 1988, SYNTHESIS-STUTTGART, P560

[2] 4,4'-DIMETHOXYTRITYL AND 4-MONOMETHOXYTRITYL TETRAFLUOROBORATE - CONVENIENT REAGENTS FOR THE PROTECTION OF PRIMARY ALCOHOLS INCLUDING SUGARS [J].

BLEASDALE, C ;

ELLWOOD, SB ;

GOLDING, BT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :803-805

[3]

BLEASDALE C, UNPUB

[4] SELECTIVE CLEAVAGE OF ALLYL ETHERS UNDER MILD CONDITIONS BY TRANSITION-METAL REAGENTS [J].

COREY, EJ ;

SUGGS, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) :3224-3224

[5]

FISCHER A, 1985, SYNTHESIS-STUTTGART, P641

[6] ENZYMATIC OXIDATION OF ETHYL CARBAMATE TO VINYL CARBAMATE AND ITS ROLE AS AN INTERMEDIATE IN THE FORMATION OF 1, N-6-ETHENOADENOSINE [J].

GUENGERICH, FP ;

KIM, DH .

CHEMICAL RESEARCH IN TOXICOLOGY, 1991, 4 (04) :413-421

[7] SUBSTITUTED DIPHENYLMETHYL PROTECTING GROUPS IN PEPTIDE SYNTHESIS [J].

HANSON, RW ;

LAW, HD .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (DEC) :7285-&

[8] 5'-ORTHO-TRITYL GROUP PROMOTED DIRECTIVE EFFECT IN THE PREPARATION OF 2'-ORTHO-METHYLRIBONUCLEOSIDES [J].

HEIKKILA, J ;

BJORKMAN, S ;

OBERG, B ;

CHATTOPADHYAYA, J .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1982, 36 (10) :715-717

[9] CALCIUM IN LIQUID-AMMONIA FOR THE REDUCTION OF BENZYL ETHERS - MECHANISTIC CLUES DERIVED FROM CHEMOSELECTIVITY STUDIES [J].

HWU, JR ;

CHUA, V ;

SCHROEDER, JE ;

BARRANS, RE ;

KHOUDARY, KP ;

WANG, N ;

WETZEL, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) :4731-4733

[10]

IMURA N, 1968, CHEM PHARM BULL, V16, P1105

← 1 2 3 →