Premium
Synthesis of glucose phosphate derivatives by the phosphite triester method
Author(s) -
ChuanZhong Tu,
ShaoPei Cai,
ZaiWan Yang
Publication year - 1984
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19840020214
Subject(s) - chemistry , phosphate , isopropyl , amine gas treating , methanol , yield (engineering) , medicinal chemistry , reagent , organic chemistry , nuclear chemistry , materials science , metallurgy
Synthesis of sugar phosphate derivatives by means of phosphite triester method is described. Seven glucose phosphotriester derivatives have been prepared, i.e. dimethyl, methyl n ‐propyl, and methyl isopropyl (1, 2:5, 6‐di‐ O ‐isopropylidene‐α‐ D ‐glucofuranose‐3‐) phosphate (5, 7 and 8); methyl bis‐(1, 2:5, 6‐di‐ O ‐isopropylidene‐α‐ D ‐glucofuranose‐3‐) phosphate (6); methyl bis‐(1, 2, 3, 4‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranose‐6‐) phosphate (9); methyl bis‐(1, 2‐ O ‐isopropylidene‐3,5‐ O ‐benzylidene‐α‐ D ‐glucofuranose‐6‐) phosphate (10); and methyl (1, 2, 5, 6‐di‐ O ‐iso‐propylidene‐α‐ D ‐glucofuranose‐3‐) (1, 2, 3, 4‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranose‐6‐) [phosphate (11). The results of the displacement of second chlorine atom of the reagent by different alcohols showed that methanol, n ‐propanol, isopropanol and as well as the glucose derivatives reacted normally to give the expected phosphite esters which yield the expected phosphate products after oxidation, but not the t ‐butanol. Removal of methyl group from a phosphotriester linkage can be easily achieved by the action of t ‐butyl amine and thus, t ‐butyl ammonium bis‐(1, 2:5, 6‐di‐ O ‐isopropylidene‐α‐ D ‐glucofuranose‐3‐) phosphate t ‐butyl amine salt (12) has been obtained from its parent phosphotriester in nearly quantitative yield. The mass spectra data of di‐ O ‐isopropylideneglucose phosphate reveals that the cleavage of these compounds follows a general pattern and can be used for their characterization.