212266-52-9

Upstream product

• 212266-43-8 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 212266-49-4 Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 212266-42-7 2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 212266-50-7 Acetic acid (2R,3S,4R,6R)-4-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 212266-51-8 Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester 

Downstream Products

• 212266-55-2 C₄₅H₆₀O₂₀ 
• 212266-54-1 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside 
• 212266-53-0 Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

The synthesis of the 2- and 2′-monodeoxygenated analogues of β-maltosyl-(1→4)-trehalose

Two derivatives of β-maltosyl-(1→4)-trehalose monodeoxygenated at C-2 or C-2′ have been synthesized in [2+2] block syntheses. N-Iodosuccinimide-mediated coupling of tetra-O-benzyl-glucose to tri-O-acetyl-D-glucal followed by O-acetylation furnished 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (7), which was used as a starting material for both tetrasaccharides. For the preparation of the 2′-monodeoxygenated saccharide the deoxyiodo pyranose moiety of 7 was further elaborated by de-O-acetylation, O-benzylidenation, O-benzylation, and selective reductive opening of the benzylidene acetal to give glycosyl acceptor 10. Glycosylation with hepta-O-acetylmaltosyl bromide and deprotection including removal of the iodo substituent afforded the 2′-deoxymaltosyl-(1→4)-trehalose 14. On the other hand, the non-iodinated pyranose moiety of 7 was transformed to a glycosyl acceptor. The removal of the benzyl groups of 7 necessitated also the reduction of the iodo group at this early stage. The resulting 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranosyl α-D-glucopyranoside was subjected to a similar reaction sequence as above to finally result in the 2-deoxymaltosyl-(1→4)-trehalose 22.