PHOTOSENSITIVE PROTECTING GROUPS OF AMINO-SUGARS AND THEIR USE IN GLYCOSIDE SYNTHESIS - 2-NITROBENZYLOXYCARBONYLAMINO AND 6-NITROVERATRYLOXYCARBONYLAMINO DERIVATIVES
PHOTOSENSITIVE PROTECTING GROUPS OF AMINO-SUGARS AND THEIR USE IN GLYCOSIDE SYNTHESIS - 2-NITROBENZYLOXYCARBONYLAMINO AND 6-NITROVERATRYLOXYCARBONYLAMINO DERIVATIVES
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DOI：
10.1021/jo00916a015
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发表时间：
1974-01-01
影响因子：
3.6
通讯作者：
PATCHORN.A
中科院分区：
文献类型：
--
作者：
AMIT, B;ZEHAVI, U;PATCHORN.A
2-Nitrobenzyloxycarbonyl and 6-nitroveratryloxycarbonyl derivatives of 2-amino-2-deoxy-D-glucose and of 2-amino-2-deoxy-D-galactose were prepared and characterized. 2-Deoxy-2-(2-nitrobenzyl6xycarbohyl) amino-1, 3, 4, 6-tetra-O-acetyl-D-glucopyranose was prepared by acetylation in pyridine and was converted by hydrogen chloride in acetic acid to the 1-chloro derivative (under the same conditions a benzyloxycarbonyl group is re-moved). The latter compound was condensed with methanol, using mercuric cyanide, to yield methyl 2-deoxy-2-(2-nitrobenzyloxycarbonyl) amino-3, 4, 6-tri-0-aCetyl-dD-glucopyranoside. Irradiation of the 2-nitrobenzyloxycarbonyl and the 6-nitroveratryloxycarbonyl derivatives afforded thefree amino derivatives in high yields. Polymer-bound aldehyde reagents were used in some of these photochemical reactions.
