A CONVENIENT PROCEDURE FOR THE DEOXYGENATION AND HOMOLOGATION OF D-RIBOSE DERIVATIVES

被引：37

作者：

ATTWOOD, SV ^{[1
]}

BARRETT, AGM ^{[1
]}

机构：

[1] UNIV LONDON IMPERIAL COLL SCI & TECHNOL, DEPT CHEM, LONDON SW7 2AY, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1984年 / 06期

关键词：

D O I：

10.1039/p19840001315

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-O-Acetyl- and 5-O-diphenyl-tert-butylsilyl-2,3-di-O-acetyl-D-ribonolactones were converted into the corresponding 3-deoxy-2-O-acetyl-D-arabinolactone derivatives 9a and 9b by sequential reaction with 1,8-diazabicyclo[5.4.0]undec-7-ene and hydrogen over palladium on carbon. Reaction of 9a and 9b with sodium borohydride, 2,4,6-tri-isopropylbenzenesulfonyl chloride and potassium cyanide in sequence respectively gave the (3S,5S)-nitriles [XCH2CH(OH)CH2CH(OH)CH2CN (X = CN and X = Ph2ButSiO)]. The latter was hydrolysed and silylated to produce (4S,6S)-4-dimethyl-tert-butylsilyloxy-6-[(dimethyl-tert-butylsilyloxy)methyl]tetrahydro-2H-pyran-2-one.

引用

页码：1315 / 1322

页数：8

共 16 条

[1] AVERMECTINS - STRUCTURE DETERMINATION [J].

ALBERSSCHONBERG, G ;

ARISON, BH ;

CHABALA, JC ;

DOUGLAS, AW ;

ESKOLA, P ;

FISHER, MH ;

LUSI, A ;

MROZIK, H ;

SMITH, JL ;

TOLMAN, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) :4216-4221

[2] STUDIES ON THE NACTINS - TOTAL SYNTHESIS OF (+/-)-TERT-BUTYL 8-O-(TERT-BUTYLDIMETHYLSILYL)NONACTATE [J].

BARRETT, AGM ;

SHETH, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :5017-5022

[3]

BARRETT AGM, 1982, J CHEM SOC CHEM COMM, V170

[4] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[5] STEREOSPECIFIC, TOTAL SYNTHESIS OF THROMBOXANE B2 [J].

HANESSIAN, S ;

LAVALLEE, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (03) :562-565

[6] PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].

HANESSIAN, S ;

LAVALLEE, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977

[7]

HANESSIAN S, 1973, TETRAHEDRON LETT, P355

[8] STEREOCHEMISTRY OF 2,4-DISUBSTITUTED-GAMMA-BUTYROLACTONES AND 2,3-DISUBSTITUTED-GAMMA-BUTYROLACTONES [J].

HUSSAIN, SAMT ;

OLLIS, WD ;

SMITH, C ;

STODDART, JF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (15) :1480-1492

[9] A METHOD FOR THE SUPPRESSION OF SELECTIVE-POPULATION TRANSFER EFFECTS IN NOE DIFFERENCE SPECTRA [J].

NEUHAUS, D .

JOURNAL OF MAGNETIC RESONANCE, 1983, 53 (01) :109-114

[10]

PERRIN DD, 1966, PURIFICATION LABORAT

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