277310-81-3

Basic information

• Product Name: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• Synonyms: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• CAS NO: 277310-81-3
• Molecular Weight: 489.5
• Mol File: 277310-81-3.mol

Chemical Properties

• CAS DataBase Reference: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride(277310-81-3)
• EPA Substance Registry System: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride(277310-81-3)

Safety Data

• Hazardous Substances Data: 277310-81-3(Hazardous Substances Data)

Upstream product

• 344403-89-0 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 
• 344403-87-8 2-[(2S,3R,4R,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 72858-55-0 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 218961-08-1 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 208644-70-6 phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 344403-86-7 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 344403-88-9 2-[(2R,4aR,6S,7R,8R,8aS)-6-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 

Downstream Products

• 344597-17-7 N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid allyl ester 
• 344597-16-6 O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-glucopyranosyl azide 
• 344597-15-5 O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 277757-07-0 phenyl O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-glucopyranosyl)-(1->6)-2,4-di-O-benzyl-3-O-(tert-butyldiphenylsilyl)-1-thio-α-D-mannopyranoside 

Relevant articles and documents

Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit

The extracellular Ig domain I of Emmprin (34-94) carrying a chitobiose unit at Asn44 was chemically synthesized. Boc-Asn with a benzyl-protected chitobiose unit was synthesized and used for the preparation of peptide thioester with the sequence of Emmprin (34-58) by Boc strategy. C-Terminal peptide amide (59-94) was also prepared by the solid-phase method. These segments were condensed by activation of the thioester group by silver ions to obtain a protected form of Emmprin (34-94)-NH2. After deprotection and air oxidation, the desired Emmprin (34-94)-NH2 with chitobiose was successfully obtained.

Attempted synthesis of type-A inositolphosphoglycan mediators - Synthesis of a pseudohexasaccharide precursor

A block synthesis approach to the inositol-containing pseudohexasaccharide 1 is presented. The myo-inositol building block 6 has been prepared using a key regioselective acylation through a boron-tin exchange reaction and the 2-azido-2-deoxy glycosyl donors 15 and 17 have been synthesized from D-glucosamine using a diazo transfer reaction. The anomeric position of the mono- and disaccharide building blocks has been temporarily protected as phenyl thioglycoside and this function was then converted into the different leaving groups to perform the glycosylation reactions. Both trichloroacetimidates and fluorides have been used as glycosyl donors for the construction of the different glycosidic linkages. The protected pseudohexasaccharides 44, 48-50, which are precursors of pseudohexasaccharide 1, have been efficiently prepared and fully characterized. Pseudohexasaccharide 1 contains the fundamental structural features which have been proposed for type A inositolphosphoglycans, which may be involved in the insulin-signaling process.