212266-45-0

Basic information

• Product Name: (2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-7-iodo-2-phenyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine
• Synonyms: (2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-7-iodo-2-phenyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS NO: 212266-45-0
• Molecular Weight: 990.929
• Mol File: 212266-45-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-7-iodo-2-phenyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-7-iodo-2-phenyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine(212266-45-0)
• EPA Substance Registry System: (2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-7-iodo-2-phenyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine(212266-45-0)

Safety Data

• Hazardous Substances Data: 212266-45-0(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 212266-42-7 2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 212266-46-1 3,6-di-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

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.