chapter  33
10 Pages

Synthesis of N-(4-Methoxybenzyl)-2-(α-d-glucopyranosyl) acetamide

Experimental Methods ........................................................................................... 258 General Methods ............................................................................................... 258

N-(4-Methoxybenzyl)-2-(2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl) acetamide (3) ................................................................................................ 258 N-(4-Methoxybenzyl)-2-(α-d-glucopyranosyl)acetamide (4) ...................... 259

Acknowledgments ..................................................................................................260 References ..............................................................................................................266

It is a thermodynamically driven process whereby large ice crystals grow larger at the expense of smaller ice crystals through the process of Ostwald ripening.1-4 During the cryopreservation of biological materials, ice recrystallization can cause extensive cell damage resulting in reduced post-thaw cell viability.5-9 Conventional cryoprotectants promote dehydration of a cell during freezing but fail to protect against cellular damage caused by ice recrystallization, which would be a bene- cial property.5,10-12 C-linked glycoproteins, synthetic analogues of antifreeze glycoproteins, have been shown to possess potent ice recrystallization inhibition (IRI) activity and also function as cryoprotectants.13-15 However, these compounds are large-molecular-weight materials. Recently, it was discovered that structurally different classes of carbohydrate-based small molecules possess IRI activity16-20 and that a crucial balance between hydrophobic and hydrophilic interactions is essential for IRI activity.19,21 Therefore, the general synthesis of small molecule IRIs like carbon-linked N-(4-methoxybenzyl)-2-(α-d-glucopyranosyl)acetamide (4) is an ef- cient method to couple hydrophobic and hydrophilic functionalities when designing IRI active small molecules.