STANNYLENE MEDIATED CHEMOSELECTIVITY .10. ALTERNATIVE SYNTHESES OF L-(-)-OLEANDROSE FROM L-RHAMNOSE PREPARATION OF GLYCALS

被引：33

作者：

BREDENKAMP, MW

HOLZAPFEL, CW

TOERIEN, F

机构：

[1] Department of Chemistry and Biochemistry, Randa Afrikaans University, Johannesburg, P.O. Box 524

来源：

SYNTHETIC COMMUNICATIONS | 1992年 / 22卷 / 17期

关键词：

D O I：

10.1080/00397919208021642

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oleandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl alpha-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).

引用

页码：2459 / 2477

页数：19

共 44 条

[1] AVERMECTINS - STRUCTURE DETERMINATION
ALBERSSCHONBERG, G
ARISON, BH
CHABALA, JC
DOUGLAS, AW
ESKOLA, P
FISHER, MH
LUSI, A
MROZIK, H
SMITH, JL
TOLMAN, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) : 4216 - 4221
[2] DERIVATIVES OF 6-DEOXY-L-TALOSE AND THE SYNTHESIS OF 6-DEOXY-2-O-(ALPHA-L-RHAMNOPYRANOSYL)-L-TALOSE
ASPINALL, GO
TAKEO, K
[J]. CARBOHYDRATE RESEARCH, 1983, 121 (SEP) : 61 - 77
[3] APPROACHES TO AVERMECTIN ASSEMBLY - ELABORATION OF AN ALPHA-L-OLEANDROSYL-ALPHA-L-OLEANDROSIDE DERIVATIVE
BARRETT, AGM
MILLER, TA
[J]. TETRAHEDRON LETTERS, 1988, 29 (16) : 1873 - 1874
[4] BIOSYNTHESIS OF CARDIAC-GLYCOSIDES - NUCLEOTIDE-BOUND 2,6-DIDEOXY-3-O-METHYLHEXOSES IN LEAF EXTRACTS OF NERIUM OLEANDER
BAUER, P
KOPP, B
FRANZ, G
[J]. PLANTA MEDICA, 1984, 50 (01) : 12 - 14
[5] SYNTHESIS OF 4-ORTHO-ALPHA-L-RHAMNOPYRANOSYL-L-RHAMNOPYRANOSE
BEBAULT, GM
DUTTON, GGS
WARFIELD, CK
[J]. CARBOHYDRATE RESEARCH, 1974, 34 (01) : 174 - 179
[6] A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF DL-OLEANDROSE
BERTI, G
CATELANI, G
COLONNA, F
MONTI, L
[J]. TETRAHEDRON, 1982, 38 (20) : 3067 - 3072
[7] BEYERMAN HC, 1965, RECL TRAV CHIM PAY-B, V84, P203
[8] BEYERMAN HC, 1963, J CHEM SOC, P755
[9] BREDENKAMP MW, 1991, S AFR J CHEM-S-AFR T, V44, P97
[10] BREDENKAMP MW, UNPUB

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