Abstract
4-O-Benzyl-23-O-isopropylidene-L-threose readily available from L-tartaric acid is a quite useful four-carbon building block for monosaccharide synthesis. The versatility can be reinforced by the coupled use of stereoselective addition reactions where the suitable choice of organometallics leads to highly anti-selective additions. The building block is particularly useful in the synthesis of rare sugars the versatility of which is demonstrated by the synthesis of some L-sugars as well as the formal total synthesis of polyoxin J in convergent manner.
| Original language | English |
|---|---|
| Pages (from-to) | 265-276 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 46 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1990 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
4-O-Benzyl-23-O-isopropylidene-L-threose : A useful building block for stereoselective synthesis of monosaccharides. / Mukaiyama, Teruaki; Suzuki, Keisuke; Yamada, Tohru; Tabusa, Fujio.
In: Tetrahedron, Vol. 46, No. 1, 1990, p. 265-276.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 4-O-Benzyl-23-O-isopropylidene-L-threose
T2 - A useful building block for stereoselective synthesis of monosaccharides
AU - Mukaiyama, Teruaki
AU - Suzuki, Keisuke
AU - Yamada, Tohru
AU - Tabusa, Fujio
PY - 1990
Y1 - 1990
N2 - 4-O-Benzyl-23-O-isopropylidene-L-threose readily available from L-tartaric acid is a quite useful four-carbon building block for monosaccharide synthesis. The versatility can be reinforced by the coupled use of stereoselective addition reactions where the suitable choice of organometallics leads to highly anti-selective additions. The building block is particularly useful in the synthesis of rare sugars the versatility of which is demonstrated by the synthesis of some L-sugars as well as the formal total synthesis of polyoxin J in convergent manner.
AB - 4-O-Benzyl-23-O-isopropylidene-L-threose readily available from L-tartaric acid is a quite useful four-carbon building block for monosaccharide synthesis. The versatility can be reinforced by the coupled use of stereoselective addition reactions where the suitable choice of organometallics leads to highly anti-selective additions. The building block is particularly useful in the synthesis of rare sugars the versatility of which is demonstrated by the synthesis of some L-sugars as well as the formal total synthesis of polyoxin J in convergent manner.
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UR - http://www.scopus.com/inward/citedby.url?scp=0001078307&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)97597-0
DO - 10.1016/S0040-4020(01)97597-0
M3 - Article
VL - 46
SP - 265
EP - 276
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 1
ER -