Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers

Table 2

Debenzylation of LGTBE 2,3,4-tri-O-benzyl (LGTBE) with 2,4-di-O-benzyl-3-O-octadecyl 1,6-anhydro--D-glucopyranose LGDBE3-18^a.

Number	Benzylated polymer					Free polymer
	Proportion		wt		[]D^25	wt	Yield		LGDBE3-18 units
	LGTBE	LGDBE-18	g	×10^3	deg	g	(%)	×10^3	mol%^e
1	98.7	1.3	0.315	83.5	+111.2	0.115	64.9	nd^d	2.8
2	96.8	3.2	0.4	117.6	+111.6	0.116	51.7	nd	4.7
3	77.8	22.2	0.367	112.5	+101.2	0.177	85.9	nd	15.7

Condition: Na; 0.4 g, solvent: liq. NH₃; 50 mL, time: 90 min, temp.: −78°C.
^bCalculated by CHCl₃ GPC.
^cCalculated by aqueous GPC.
^dInsoluble in water.
^eCalculated from ¹H NMR spectrum in DMSO-d₆.