209911-76-2

Upstream product

• 209911-52-4 allyl 3-O-benzyl-D-glucopyranoside 
• 76-83-5 trityl chloride 
• 100-39-0 benzyl bromide 
• 209911-73-9 1-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-bis-O-<(4-methoxyphenyl)methyl>-3,5-bis-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucitol 
• 209911-72-8 1-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-bis-O-<(4-methoxyphenyl)methyl>-3-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucitol 
• 209911-75-1 2,4-bis-O-<(4-methoxyphenyl)methyl>-3,5-bis-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucose 
• 209911-74-0 2,4-bis-O-<(4-methoxyphenyl)methyl>-3,5-bis-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucitol 
• 209911-59-1 2-propenyl 2,4-bis-O-<(4-methoxyphenyl)methyl>-3-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucopyranoside 
• 209911-67-1 2,4-bis-O-<(4-methoxyphenyl)methyl>-3-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucitol 
• 209911-56-8 2-propenyl 3-O-(phenylmethyl)-6-O-(triphenylmethyl)-D-glucopyranoside 
• 225377-53-7 1,1-dibromo-3,5-bis-O-<(4-methoxyphenyl)methyl>-4,6-bis-O-(phenylmethyl)-7-O-(triphenylmethyl)-D-gluco-hept-1-enitol 

Downstream Products

• 104873-76-9 2,3,6-tris-O-(phenylmethyl)-D-myo-inositol 
• 145789-66-8 1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-myo-inositol 
• 209911-80-8 (3S,4R,5S,6S)-2-ethenylidene-3,5-bis-<(4-methoxyphenyl)methoxy>-4,6-bis(phenylmethoxy)cyclohexanone 
• 209911-78-4 1,2,3-trideoxy-4,6-bis-O-<(4-methoxyphenyl)methyl>-5,7-bis-O-(phenylmethyl)-1-(trimethylsilyl)-D-gluco-oct-2-ynitol 
• 209911-44-4 6,7,8-trideoxy-3,5-bis-O-<(4-methoxyphenyl)methyl>-2,4-bis-O-(phenylmethyl)-8-(trimethylsilyl)-L-gulo-oct-6-ynose 
• 209911-85-3 1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-epi-4-inosose 
• 209911-83-1 4-deoxy-4-ethenylidene-1,5-bis-O-<(4-methoxyphenyl)methyl>-2,3,6-tris-O-(phenylmethyl)-D-myo-inositol 
• 209911-81-9 4-deoxy-4-ethenylidene-1,5-bis-O-<(4-methoxyphenyl)methyl>-2,6-bis-O-(phenylmethyl)-D-myo-inositol 
• 209911-79-5 5-deoxy-5-ethenylidene-2,4-bis-O-<(4-methoxyphenyl)methyl>-1,3-bis-O-(phenylmethyl)-L-chiro-inositol 
• 209911-77-3 1,2,3-trideoxy-4,6-bis-O-<(4-methoxyphenyl)methyl>-5,7-bis-O-(phenylmethyl)-1-(trimethylsilyl)-8-O-(triphenylmethyl)-D-gluco-oct-2-ynitol 

Relevant academic research and scientific papers

Formal synthesis of D-myo-inositol 1,4,5-tris(dihydrogen phosphate): Cyclization by an unusual ene reaction and use of the Bu2SnCl2/Bu2SnH2 reagent for generating an equatorial alcohol

D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).

A synthetic route from D-glucose to D-myo-inositol-1,4,5- tris(dihydrogenphosphate): Use of an unusual ene reaction and the Bu2SnCl2/Bu2SnH2 reagent

D-Glucose was converted into the propargylsilane aldehyde 3, which underwent ring closure with retention of silicon, in the presence of camphorsulfonic acid, to give 5, and this was elaborated, via ketone 22, into 2, which had previously been transformed into D-myo-inositol-1,4,5- tris(dihydrogenphosphate). A crucial step in the synthesis is the stereoselective reduction of 22 with Bu2SnCl2/Bu2SnH2, a reagent system that shows a strong preference for generating equatorial alcohols.