Abstract
An efficient and convenient synthetic route to glycosyl phosphites and phosphates has been developed that uses dibenzyl N.N-diethylphosphoramidite as a phosphitylating reagent. Glycosyl phosphites and phosphates of 2-acetamido-2-deoxy-D-galactose (GalNAc) (29), 2-acetamido-2-deoxy-D-glucose (GlcNAc) (30), D-galactose (Gal) (31), D-glucose (Glc) (32), D-mannose (Man) (33), L-rhamnose (Rha) (34), L-fucose (Fuc) (35), and N-acetylneuraminic acid (NeuAc) (41) were prepared by this procedure. Compounds 29 and 30 were obtained as α anomers exclusively, whereas compounds 31, 32, and 41 were obtained as β anomers, and compounds 33 and 34, as α anomers, predominately. The phosphates are useful for the synthesis of sugar nucleotides, and the phosphites are effective glycosylation reagents.
| Original language | English |
|---|---|
| Pages (from-to) | 2260-2267 |
| Number of pages | 8 |
| Journal | Journal of the American Chemical Society |
| Volume | 115 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Mar 1 1993 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Synthesis and Use of Glycosyl Phosphites : An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides. / Sim, Mui Mui; Kondo, Hirosato; Wong, Chi Huey.
In: Journal of the American Chemical Society, Vol. 115, No. 6, 01.03.1993, p. 2260-2267.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and Use of Glycosyl Phosphites
T2 - An Effective Route to Glycosyl Phosphates, Sugar Nucleotides, and Glycosides
AU - Sim, Mui Mui
AU - Kondo, Hirosato
AU - Wong, Chi Huey
PY - 1993/3/1
Y1 - 1993/3/1
N2 - An efficient and convenient synthetic route to glycosyl phosphites and phosphates has been developed that uses dibenzyl N.N-diethylphosphoramidite as a phosphitylating reagent. Glycosyl phosphites and phosphates of 2-acetamido-2-deoxy-D-galactose (GalNAc) (29), 2-acetamido-2-deoxy-D-glucose (GlcNAc) (30), D-galactose (Gal) (31), D-glucose (Glc) (32), D-mannose (Man) (33), L-rhamnose (Rha) (34), L-fucose (Fuc) (35), and N-acetylneuraminic acid (NeuAc) (41) were prepared by this procedure. Compounds 29 and 30 were obtained as α anomers exclusively, whereas compounds 31, 32, and 41 were obtained as β anomers, and compounds 33 and 34, as α anomers, predominately. The phosphates are useful for the synthesis of sugar nucleotides, and the phosphites are effective glycosylation reagents.
AB - An efficient and convenient synthetic route to glycosyl phosphites and phosphates has been developed that uses dibenzyl N.N-diethylphosphoramidite as a phosphitylating reagent. Glycosyl phosphites and phosphates of 2-acetamido-2-deoxy-D-galactose (GalNAc) (29), 2-acetamido-2-deoxy-D-glucose (GlcNAc) (30), D-galactose (Gal) (31), D-glucose (Glc) (32), D-mannose (Man) (33), L-rhamnose (Rha) (34), L-fucose (Fuc) (35), and N-acetylneuraminic acid (NeuAc) (41) were prepared by this procedure. Compounds 29 and 30 were obtained as α anomers exclusively, whereas compounds 31, 32, and 41 were obtained as β anomers, and compounds 33 and 34, as α anomers, predominately. The phosphates are useful for the synthesis of sugar nucleotides, and the phosphites are effective glycosylation reagents.
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U2 - 10.1021/ja00059a023
DO - 10.1021/ja00059a023
M3 - Article
VL - 115
SP - 2260
EP - 2267
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 6
ER -