Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-D-glyceraldehyde

被引：6
|
作者：
Ulgheri, F
Bacsa, J
Nassimbeni, L
Spanu, P [1 ]
机构：
[1] CNR, Ist Chim Biomol, Sez Sassari Trav La Crucca 3, I-07040 Li Punti Sassari, Italy
[2] Univ Cape Town, Dept Chem, ZA-7701 Rondebosch, South Africa
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 04期
关键词：
dihydrouracil; dihydropyrimidin-2,4-dione; glyceraldehyde;
D O I：
10.1016/S0040-4039(02)02701-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The aldol-type addition of 1,3-dibenzyl-dihydrouracil 2 to 2,3-O-isopropylidene-D-glyceraldehyde 3 was examined in different solvents and under Lewis acid catalysis in order to establish the stereochemical preferences. A stereodivergent synthesis of 5-trihydroxypropyl-dihydrouracil derivatives 4 and its C-5 epimer 5 was realized. The synthesis of ureido polyols 8 and 10 was obtained via the reductive ring opening of the templates 4 and 5. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：671 / 675
页数：5
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