205869-99-4

Basic information

• Product Name: Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester
• Synonyms: Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS NO: 205869-99-4
• Molecular Weight: 1099.1
• Mol File: 205869-99-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester(205869-99-4)
• EPA Substance Registry System: Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester(205869-99-4)

Safety Data

• Hazardous Substances Data: 205869-99-4(Hazardous Substances Data)

Upstream product

• 205869-94-9 octyl 4-O-acetyl-2-O-benzoyl-3-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 
• 205869-93-8 octyl 2-O-benzoyl-3-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 
• 205869-90-5 octyl 2,4,6-tri-O-benzoyl-3-O-benzyl-β-D-mannopyranoside 
• 205869-89-2 octyl 4,6-di-O-benzoyl-3-O-benzyl-β-D-mannopyranoside 
• 205869-83-6 1,5-anhydro-2,4,6-tri-O-benzoyl-3-O-benzyl-D-arabino-hex-1-enitol 
• 205869-91-6 octyl 2-O-benzoyl-3-O-benzyl-β-D-mannopyranoside 
• 205869-82-5 4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide 
• 30572-04-4 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-D-glucopyranoside 
• 151072-53-6 2,4,6-Tri-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl bromide 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 121238-27-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate 
• 205869-97-2 octyl 4-O-acetyl-2-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 

Downstream Products

• 140147-36-0 α-D-Manp-(1->3)-(α-D-Manp)-(1->6)-β-D-Manp-1->O(CH2)7CH3 

Relevant articles and documents

4,6-Di-O-benzoyl-3-O-benzyl-α-D-arabino-hexo-pyranos-2-ulosyl bromide: A conveniently accessible glycosyl donor for the expedient construction of diantennary β-D-mannosides branched at O-3 and O-6

A concise practical, large scale-adaptable six-step sequence has been developed for the transformation of diacetone-glucose into 4,6-di-O-benzoyl- 3-O-benzyl-α-D-arabino-hexo-pyranos-2-ulosyl bromide (7), a most useful indirect β-D-mannosyl donor as its blocking group pattern allows the construction of biologically relevant β-D-mannosides branched at O-3 and O- 6. The broad utility of this new ulosyl bromide 7 resides in its high anomeric reactivity, and in the ease and uniformity with which β- stereocontrol can be achieved over both, glycosidations and carbonyl reduction of the β-ulosides formed: Koenigs-Knorr conditions exclusively provide β-glycosiduloses, hydride reduction of their carbonyl functions proceeds with high stereoselectivities (> 20:1) in favor of the β-D- mannosides. These preparatively auspicious properties are materialized in an efficient, straightforward synthesis of α-D-Manp-(1 → 6)-[α-D-Manp-(1 → 3)]-β-D-Manp-(1 → O)-Octyl, the 3,6-O-branched core-mannotrioside carrying an octyl spacer instead of the chitobiosyl unit.