A novel photochemical synthesis of dideoxyfuranosyl disaccharides

被引：2

作者：

Angelini, MP ^{[1
]}

Lee-Ruff, E ^{[1
]}

机构：

[1] York Univ, Dept Chem, N York, ON M3J 1P3, Canada

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 48期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(98)02015-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photochemical glycosylation is described using the chiral cyclobutanone 1. Irradiation of ketone 1 in me presence of monosaccharides 2 and 3 gives photoadducts derived from OH insertion of the transient carbene. The carbene inserts into the N-H group in the case of nucleoside 4. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：8783 / 8786

页数：4

相关论文

共 21 条

[1] AN EFFICIENT AND DIASTEREOSELECTIVE [2+2] CYCLOADDITION - CONVENIENT AND ENANTIOSELECTIVE ROUTE TO TRANS-2',3'-DIHYDROXYMETHYLCYCLOBUTANE NUCLEOSIDE ANALOGS [J].

AHMAD, S .

TETRAHEDRON LETTERS, 1991, 32 (48) :6997-7000

[2]

ALBERT A, 1984, DETEMINATION IONIZAT, P124

[3] A NEW SYNTHESIS OF O-GLYCOSIDES FROM TOTALLY O-UNPROTECTED GLYCOSYL DONORS [J].

FERRIERES, V ;

BERTHO, JN ;

PLUSQUELLEC, D .

TETRAHEDRON LETTERS, 1995, 36 (16) :2749-2752

[4] NITRATE ION AS CATALYST FOR SELECTIVE SILYLATIONS OF NUCLEOSIDES [J].

HAKIMELAHI, GH ;

PROBA, ZA ;

OGILVIE, KK .

TETRAHEDRON LETTERS, 1981, 22 (48) :4775-4778

[5] METHOXYCHLOROCARBENE - MATRIX SPECTROSCOPY AND PHOTOCHEMISTRY [J].

KESSELMAYER, MA ;

SHERIDAN, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (01) :99-107

[6] SYNTHESIS OF COMPLEX NUCLEOSIDE ANTIBIOTICS [J].

KNAPP, S .

CHEMICAL REVIEWS, 1995, 95 (06) :1859-1876

[7] A NOVEL-APPROACH TOWARDS 2,3-DIDEOXYRIBOSIDE SYNTHESIS [J].

LEERUFF, E ;

JIANG, JL ;

WAN, WQ .

TETRAHEDRON LETTERS, 1993, 34 (02) :261-264

[8] Enantioselective preparation of 2',3'-dideoxynucleosides and their analogues from ring-expansion of cyclobutanones .2. Synthesis of 2',3'-dideoxyribosides and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane [J].

LeeRuff, E ;

Xi, FD ;

Qie, JH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1547-1550

[9] A NOVEL-APPROACH TOWARD THE SYNTHESIS OF CHIRAL 2,3-DIDEOXY NUCLEOSIDES AND THEIR CARBOCYCLIC ANALOGS [J].

LEERUFF, E ;

WAN, WQ ;

JIANG, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :2114-2118

[10] Synthesis and HIV inhibition activity of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides [J].

LeeRuff, E ;

Ostrowski, M ;

Ladha, A ;

Stynes, DV ;

Vernik, I ;

Jiang, JL ;

Wan, WQ ;

Ding, SF ;

Joshi, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) :5276-5280