14193-49-8

Upstream product

• 17460-41-2 methyl-[O²,O⁴,O⁶-triacetyl-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 3257-61-2 methyl 2,3-anhydro-α-D-allopyranoside 
• 60844-86-2 methyl 3-deoxy-3-methoxyimino-α-D-ribo-hexopyranoside 
• 16977-86-9 methyl-α-D-ribo-hexapyranoside-3-ulose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 97971-35-2 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-brosyl-α-D-allopyranoside 
• 97971-36-3 methyl 2-O-benzoyl-3-O-brosyl-α-D-allopyranoside 
• 97971-39-6 methyl 3-azido-2-O-benzoyl-3-deoxy-α-D-glucopyranoside 
• 56253-26-0 methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-allopyranoside 
• 14257-71-7 (2R,3S,4S,5R,6S)-4-Amino-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3,5-diol; hydrochloride 
• 5152-11-4 methyl-3-azido-3-deoxy-α-D-glucopyranoside 

Downstream Products

• 97971-33-0 methyl 4,6-O-benzylidene-3-(tert-butoxycarbonyl)amino-3-deoxy-α-D-glucopyranoside 
• 2595-38-2 Methyl-(3-acetamino-3-deoxy-2,4,6-tri-O-acetyl-α-D-glucopyranosid) 

Relevant academic research and scientific papers

Stereoselective Protection-Free Modification of 3-Keto-saccharides

Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.

Streptozotocin analogs

New 3-methyl-3-nitrosoureido derivatives of the following amino sugars were prepared as analogs of streptozotocin with the anomeric carbon protected, by nitrosating the methylureas in water with N2 O3 : 3-amino-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose; methyl 3-amino-3-deoxy-β-D-xylopyranoside; methyl 3-amino-3-deoxy-α-D-altropyranoside; methyl 3-amino-3-deoxy-α-D-glucopyranoside; and methyl 3-amino-2,3,6-trideoxy-α-L-lyxohexopyranoside. Tests against murine leukemia L1210 show that the anticancer activity of streptozotocin not only was retained but was enhanced in most of these derivatives.