131289-29-7

Upstream product

• 131289-28-6 (2S,3R,4R,5S) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 85716-45-6 1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon 

Downstream Products

• 671199-53-4 (+)-(1S,2R,3R,4S,6S)-1,2,3-tribenzyloxy-4-tert-butyldimethylsilyloxy-6-mesyloxycyclohexane 
• 671199-46-5 (4R,5S,6R)-4,5,6-tris(benzyloxy)cyclohex-2-en-1-one 
• 671199-55-6 (-)-(1S,2S,3R,4S,5R)-2,3,4-tribenzyloxy-5-mesyloxycyclohexanol 
• 121513-06-2 (1S,2S,3R,4R,5R)-2,3,4-Tris-benzyloxy-5-(tetrahydro-pyran-2-yloxy)-cyclohexanol 
• 131349-43-4 (2R)-(2,4,5/3)-2,3,4-tribenzyloxy-5-hydroxycyclohexanone 
• 121513-05-1 (2R,3S,4R,5R)-2,3,4-Tris-benzyloxy-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone 

Relevant academic research and scientific papers

Synthesis of (+)-(2R,3S,4R)-2,3,4-trihydroxycyclohexanone from D-glucose

We have described the synthesis of (+)-(2R,3S,4R)-2,3,4- trihydroxycyclohexanone by the reduction of a keto-conduritol derivative, the latter being prepared in five steps from (-)-(2S,3R,4S,5S)-2,3,4-tribenzyloxy-5- hydroxycyclohexanone, which is in turn

Hexa-O-benzyl-5-hydroxy-pseudo-α-D-glucopyranose and its C-5 epimer

(2S)-(2,4,5/3)-2,3,4-Tribenzyloxy-5-(tetrahydropyran-2-yloxy)cyclohexanone (9), when treated with vinylmagnesium bromide and trimethylsilylmethylmagnesium chloride, gave (1S)-(1O,2,4,5/1C,3)-2,3,4-tribenzyloxy-5-(tetrahydropyran-2-yloxy)-1-vinylcyclohexanol (10) and (1R)-(1O,2,4,5/1C,3)-2,3,4-tribenzyloxy-1-(trimethylsilylmethyl)cyclohexane-1,5-diol (16), respectively, with the S configuration at C-1 exclusively.Following oxidative cleavage of the double bond, 10 was converted into (1S)-(1O,2,4,5/1C,3)-1,2,3,4,5-pentabenzyloxy-1-(benzyloxymethyl)cyclohexane (14), the C-5 epimer 19 of which was obtained from the trimethylsilylmethyl-substituted adduct following hydroxylation of the double bond of the derived (2R)-(2,4,5/3)-2,3,4-tribenzyloxy-5-hydroxy-1-methylenecyclohexane (17). (2S)-(2,4,5/3)-2,3,4-Tribenzyloxy-5-hydroxycyclohexanone (7) was converted into its enantiomer 26 and into (1S)-(1O,2,4,5O/1C,5C)-2,3,4-tribenzyloxy-5-(trimethylsilyl)methyl-1-vinylcyclohexane-1,5-diol (28).