149115-58-2

Upstream product

• 144427-63-4 (Z)-1-O-acetyl-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-3-O-methyl-D-xylo-hex-5-enitol 
• 108-24-7 acetic anhydride 
• 141240-05-3 (Z)-1,3-di-O-acetyl-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol 
• 141240-06-4 (Z)-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol 
• 144427-53-2 (Z)-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol 

Downstream Products

• 141240-19-9 5,6-Dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol 
• 144427-53-2 (E)-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol 

Relevant academic research and scientific papers

Acetolysis of 2,4-O-benzylidene-D-xylo-hex-5-enitol derivatives

Acetolysis of (Z)-1-O-acetyl-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-3-O-methanesulfonyl-D-xylo-hex-5-enitol afforded (E)-1,2,4-tri-O-acetyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-3-O-methanesulfonyl-D-xylo- and -L-arabino-hex-5-enitol, 2-C--3,6-di-O-acetyl-2-deoxy-4-O-methanesulfonyl-β-L-galacto-hexopyranosylbenzene and 6-O-acetyl-2-deoxy-2-C--4-O-methanesulfonyl-β-L-galacto-hexopyranosylbenzene 3,7-(cyclic sulfate).The scope of this rearrangement was studied further on compounds with a 4-methoxybenzylidene instead of a benzylidene group, and a phenyl instead of a 2,4-dichlorophenyl group.In the latter reaction, in addition to 2-C--3,4,5-tri-O-acetyl-2-deoxy-β-L-galacto-hexopyranosylbenzene, 1(S)-2-C--1,3,4,5,6-penta-O-acetyl-2-deoxy-1-phenyl-L-gulitol was formed, the structure of which was established by X-ray analysis.

Rearrangement of unsaturated 2,4-O-benzylidenehexitol derivatives into C-glycosylbenzene derivatives

Acetolysis of (Z)-1,3-di-O-acetyl-2,4-O-benzylidene-6-C-(2,4-dichlorophenyl)-D-xylo -hex-5-enitol (3) afforded (E)-1,2,3,4-tetra-O-acetyl-6-C-(2,4-dichlorphenyl)-D-xylo-hex-5- enitol and 2-C-[(R)-acetoxy(2,4-dichlorophenyl)methyl]- 3,4,6-tri-O-acetyl-2-de