DIVERGENT AND STEREOCONTROLLED APPROACH TO THE SYNTHESIS OF URACIL NUCLEOSIDES BRANCHED AT THE ANOMERIC POSITION

被引：54

作者：

ITOH, Y ^{[1
]}

HARAGUCHI, K ^{[1
]}

TANAKA, H ^{[1
]}

GEN, E ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

[1] SHOWA UNIV,SCH PHARMACEUT SCI,SHINAGAWA KU,TOKYO 142,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 03期

关键词：

D O I：

10.1021/jo00108a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic addition of NBS/pivalic acid (bromopivaloyloxylation) to 1-[3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-erythro-pent- 1-enofuranosyl]uracil (2), readily accessible from O-2,2'-anhydro-uridine, furnished 1-[2-bromo-3,5-bis-O-(tert-butyldimethyylsilyl)-2-deoxy-1-(pivaloyloxy)-beta-D-ara-binofuranosyl]uracil (7) stereoselectively. This compound (7), having a leaving group at the 1'-position as well as 2'-beta-Br that could exert anchimeric assistance, serves as versatile intermediate for the stereocontrolled synthesis of various types of 1'-C-branched derivatives through nucleophilic substitutions by the use of organosilicon and organoaluminum reagents. The whole sequence constitutes the first example of the conversion of a naturally-occurring nucleoside to the analogues branched at the anomeric position.

引用

页码：656 / 662

页数：7

共 43 条

[11]

HARAGUCHI K, 1989, SYNTHESIS-STUTTGART, P434

[12] CLEAVAGE OF CYCLIC ETHERS INCLUDING OXETANE AND OXOLANE WITH A HIGHLY NUCLEOPHILIC SPECIES OF PHENYLSELENIDE ANION [J].

HARAGUCHI, K ;

TANAKA, H ;

HAYAKAWA, H ;

MIYASAKA, T .

CHEMISTRY LETTERS, 1988, (06) :931-934

[13] PREPARATION AND REACTIONS OF 2'-VINYL AND 3'-VINYL BROMIDES OF URACIL NUCLEOSIDES - VERSATILE SYNTHONS FOR ANTI-HIV AGENTS [J].

HARAGUCHI, K ;

ITOH, Y ;

TANAKA, H ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1991, 32 (28) :3391-3394

[14] ANOMERIC MANIPULATION OF NUCLEOSIDES - STEREOSPECIFIC ENTRY TO 1'-C-BRANCHED URACIL NUCLEOSIDES [J].

HARAGUCHI, K ;

ITOH, Y ;

TANAKA, H ;

YAMAGUCHI, K ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1993, 34 (43) :6913-6916

[15] SELENOXIDE ELIMINATION FOR THE SYNTHESIS OF UNSATURATED-SUGAR URACIL NUCLEOSIDES [J].

HARAGUCHI, K ;

TANAKA, H ;

MAEDA, H ;

ITOH, Y ;

SAITO, S ;

MIYASAKA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5401-5408

[16] STEREOSELECTIVE SYNTHESIS OF 4'-C-BRANCHED 2',3'-DIDEHYDRO-2',3'-DIDEOXY NUCLEOSIDES BASED ON SNCL4-PROMOTED ALLYLIC REARRANGEMENT [J].

HARAGUCHI, K ;

TANAKA, H ;

ITOH, Y ;

SAITO, S ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1992, 33 (20) :2841-2844

[17] ADDITION OF CARBON RADICALS TO 4',5'-UNSATURATED URACILNUCLEOSIDES BY THE USE OF ORGANOSELENIUM REAGENTS - A NEW STEREOSELECTIVE ENTRY TO C-C BOND FORMATION AT THE 5'-POSITION [J].

HARAGUCHI, K ;

TANAKA, H ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1990, 31 (02) :227-230

[18]

HARAGUCHI K, 1993, TETRAHEDRON, V42, P1371

[19]

HARAGUCHI K, 1991, TETRAHEDRON LETT, V32, P770

[20] A RIBONOLACTONE-BASED APPROACH TO THE SYNTHESIS OF 1'-CARBON-SUBSTITUTED THYMINE RIBONUCLEOSIDES [J].

HAYAKAWA, H ;

MIYAZAWA, M ;

TANAKA, H ;

MIYASAKA, T .

NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (1-3) :297-308

← 1 2 3 4 5 →