1 -Thio-a-D-glucopyranose

Reaction of peracetylated 1-thio-a-D-glucopyranose (10a) with peracetylated 6-deoxy-6-iodomaltose (18), 6 -deoxy-6 -iodomaltose (21a) and 6 -deoxy-6 -iodomalto-oligosaccharides (21 b, 21 c) gave the corresponding S-a-glucosylthio-maltose derivatives (20,23a-c) in excellent yields (Scheme 7) [24,28,29a]. 

The first reported synthesis of peracetylated 1-thio-a-D-glucopyranose started from the Brigl s anhydride [9] but traditionally, 1,2-cw-thioglycoses have been generated from the 1,2-tranj-glycosyl halides by reaction of alkyl or benzyl xanthates in acetone [13], potassium thioacetate in hexamethylphosphoramide (HMPA) [14], or the tetrabutylammonium salt of thioacetic acid in toluene [15] (Scheme 1). A recent alternative is the peroxide-induced addition of thioacetic acid to hydroxy-glucal derivatives [16]. 

This preparation, specifically of acylated aryl thioglycosides, is carried out by reaction of, for instance, a 2,3,4,6-tetra-O-acety 1-1 -thio-P-D-glucopyranose with a di-azonium salt, followed by thermal decomposition of the intermediate diazo product. 

The first syntheses of 1,2-cfs-thioglycoses (a-D-gluco- and )3-D-manno- derivatives) have been achieved by the reaction in acetone of alkyl or benzyl xanthate or potassium thioacetate with the corresponding l,2-tra s-glycosyl halides [13]. More recently, tetra-O-acetyl-l-S-acetyl-l-thio-a-D-glucopyranose (10a) (Scheme 3) has been obtained i) by reaction of -acetochloroglucose (9 a) with either potassium thioacetate in HMPA or the tetrabutylammonium salt of thio-acetic acid in toluene [14] ii) by peroxide-induced addition of thioacetic acid to the pseudo-glucal (11) [15]. 

Penta-Ac 1,2,3,4,6-Pentaacetyl-l-thio-a-D-glucopyranose. 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-l-thio-a-D-glucopyranose [62860-10-0]... 

Thio-p-D-glucopyranose l-[3-hydroxy-3-methyl-A -(sulfooxy)butanimidate], H-177... 

I-Thio-p-D-glucopyranose l-[4-hydroxy-A-(sulfooxy)pentanimidate], H-134 1-Thio-p-D-glucopyranose l-[5-hydroxy-i -(sulfooxy)pentanimidate], H-135 1-Thio-p-D-glucopyranose l-[3-hydroxy-i r-(sulfooxy)-4-pentenimidate], P-94 1-Thio-p-D-glucopyranose l-[3-hydroxy-i -(sulfooxy)propanimidate], H-139 1-Thio-p-D-glucopyranose l-[5-methoxy-5-oxo-i -(sulfooxy)pentanimidate], M-140... 

Acetamido-1,2,3,6-tetra-O -acetyl-4-deoxy-p-D-glucopyranose, A-268 6-Acetamido-1,2,3,4-tetra-O -acetyl-6-deoxy-a-D-glucopyranose, A-270 6-Acetamido-1,2,3,4-tetra-O-acetyl-6-deoxy-p-D-glucopyranose, A-270 2-Acetamido-1,3,4,6-tetra-O -acetyl-2-deoxy-5-thio-a-D-glucopyranose,... 

Acetamido-3,4,6-tri-0-acetyl-2-deoxy-p-D-glucopyranosyl azide, A-222 2-Acetamido-3,4,6-1 ri- O -acetyl-2-deoxy-1 -thio- p-D-glucopyranose. A- 347... 

Pentaacetyl-l-thio-a-D-glucopyranose, T-70 Penta-O-acetyl-l-thio-p-D-glucopyranoside, T-70... 

---