180182-68-7

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 179992-23-5 Methyl 3,4-di-O-benzoyl-2-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 
• 1055037-79-0 Benzoic acid (2S,3R,4S,5S,6S)-3-benzyloxy-6-bromomethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester 
• 147514-07-6 Methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 147425-46-5 methyl 3‐O‐benzoyl‐2‐O‐benzyl‐α‐D-glucopyranoside 
• 180182-67-6 (2S,3R,4S,5R)-2,3-Dibenzoyloxy-4-benzyloxy-5-hydroxycyclohexanone 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1054616-82-8 C₂₈H₂₇IO₇ 
• 179992-22-4 Methyl 3,4-di-O-benzoyl-2-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside 

Downstream Products

• 180182-69-8 L-1-O-Benzyl-3-deoxy-scyllo-inositol 
• 1054617-94-5 Phosphorous acid (1R,2S,3R,4R,5S)-2-benzyloxy-3,4,5-tris-[bis-(4-chloro-benzyloxy)-phosphanyloxy]-cyclohexyl ester bis-(4-chloro-benzyl) ester 

Relevant academic research and scientific papers

Synthesis of D-2-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate from D-glucose

A route to a novel, structurally modified D-myo-inositol 1,3,4,5-tetrakisphosphate analogue, D-2-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate 3, is described, involving as the key steps a selective protection of methyl α-D-glucopyranoside and subsequent catalytic Ferrier rearrangement to a deoxyinosose. Thus, methyl α-D-glucopyranoside was converted by an improved procedure into methyl 4,6-O-benzylidene-α-D-glucopyranoside 4 and thence into methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 7 without recourse to column chromatography. Compound 7 was converted into methyl 3,4-di-O-benzoyl-2-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 12 via methyl 3,4-di-O-benzoyl-2-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside 8. Rearrangement of enol ether 12 with mercury(II) trifluoroacetate provided (2S,3R,4S,5R)-2,3-dibenzoyloxy-4-benzyloxy-5-hydroxycyclohexanone 13 and (2S,3A,4S,5S)-2,3-dibenzoyloxy-4-benzyloxy-5-hydroxycyclohexanone 14. Attempts to invert the configuration at position 5 of compound 14 were unsuccessful, but provided a number of discrete products. Reduction of compound 13 and saponification furnished L-1-O-benzyl-3-deoxy-scyll-inositol 23, which was phosphorylated and deprotected to give the target 3.