186820-62-2

Upstream product

• 186820-64-4 (2R,4aR,6S,8S,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-7-one 
• 19488-49-4 methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 142789-96-6 1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose 

Downstream Products

• 186820-78-0 (1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol 
• 186820-75-7 (1R,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol 
• 186820-66-6 (2R,4aR,6R,8S,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-7-one 
• 186820-68-8 (2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-7-ol 
• 186820-74-6 (2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxine 
• 186820-77-9 (2R,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanone 
• 186820-64-4 (2R,4aR,6S,8S,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-7-one 

Relevant academic research and scientific papers

Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides

This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioe

Synthesis of methyl 5a′-carba-β-lactoside and N-acetyl-5a′-carba-β-lactosaminides, and related 5a′-carbadisaccharides

Construction of the ether-linked methyl 5a′-carba-β-lactoside (3) and N-acetyl-5a′-carba-β-lactosaminide (4) were carried out starting from the coupling products 15 and 16, readily obtained by coupling between 1,2-anhydro-4,6-O-benzylidene-5a-carba-D-mannopyranose (7) and the oxide anions generated from methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (8) and methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (10), respectively. Their 5a-carba-α-D-mannopyranose moieties were transformed into those of 5a-carba-β-D-galactopyranose by a sequence of reaction: Oxidation of the 2′-OH group, epimerization of the C-1′ with DBU, selective reduction of the carbonyl group, and epimerization of the C-4′ via oxidation and then reduction of 4′-OH or SN2 reaction of the 4′-mesylate with an acetate anion. Reaction of 1,2-anhydro-6-O-benzyl-3,4-O-isopropylidene-5a-carba-α-D-galactopyranose (6), initially expected as the potential donor, with these oxide anions did not give any ether-linked products, rather resulting in elimination reaction of 7. However, coupling of the epoxide 6 with methyl 2-acetamido-4-amino-2,4-dideoxy-β-D-glucopyranosides (19) easily gave rise to imino-linked 5a′-carbadisaccharide derivative 38, which, after deprotection, gave the imino-linked congener 5. On the other hand, two biologically interesting carbadisaccharides including methyl N,N′-diacetyl-5a′-carbachitobioside (45) were obtained from the versatile intermediate 24.