340290-26-8

Basic information

• Product Name: tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside
• Synonyms: tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside
• CAS NO: 340290-26-8
• Molecular Weight: 715.916
• Mol File: 340290-26-8.mol

Chemical Properties

• CAS DataBase Reference: tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside(340290-26-8)
• EPA Substance Registry System: tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-phenoxyacetyl-β-D-glucopyranoside(340290-26-8)

Safety Data

• Hazardous Substances Data: 340290-26-8(Hazardous Substances Data)

Upstream product

• 701-99-5 Phenoxyacetyl chloride 
• 216877-47-3 tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside 

Downstream Products

• 340290-38-2 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate 
• 340290-29-1 tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 340290-41-7 benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 340290-30-4 tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 340290-42-8 benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 
• 340290-39-3 benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D-glucopyranoside 
• 340290-40-6 benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection

tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside was readily transformed into the disaccharide glycosyl donor, 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl- (1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-α/β-D- glucopyranosyl trichloroacetimidate, and the disaccharide glycosyl acceptor, tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl- (1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D- glucopyranoside. A TMSOTf-catalysed coupling of the acceptor with the donor afforded the respective tetrasaccharide derivative, which can be transformed to chitotetraose. tert-Butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D- glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- β-D-glucopyranoside was converted into donor 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-4-O-phenoxyacetyl-β-D- glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- β-D-glucopyranosyl trichloroacetimidate. Its coupling with benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl- (1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D- glucopyranoside, followed by dephenoxyacetylation, gave benzyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl- (1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D- glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido- β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2- dimethylmaleimido-β-D-glucopyranoside, whose glycosylation furnished, after replacement of the DMM-group by the acetyl moiety and subsequent deprotection, chitohexaose.