121513-06-2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 85716-45-6 1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon 
• 131289-29-7 (+)-(1R,2R,3S,4R,5S)-2,3,4-tribenzyloxy-5-(tert-butyldimethylsilyloxy)cyclohexanol 
• 131289-28-6 (2S,3R,4R,5S) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one 
• 121513-05-1 (2S,3R,4S,5R)-2,3,4-Tris-benzyloxy-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone 
• 87984-31-4 (2S,3R,4S,5R) 5-hydroxy-2,3,4-tris(benzyloxy) cyclohexane-1-one 
• 121513-05-1 (2S)-(2,4,5/3)-2,3,4-tribenzyloxy-5-(tetrahydropyran-2-yloxy)cyclohexanone 

Downstream Products

• 131349-43-4 (2R)-(2,4,5/3)-2,3,4-tribenzyloxy-5-hydroxycyclohexanone 
• 121513-08-4 Butyric acid (1R,2R,3R,4S,5S)-2,3,4-tris-benzyloxy-5-hydroxy-cyclohexyl ester 
• 118190-49-1 (5R,5aR,9S)-9-((1S,2R,3S,4R,5S)-5-Amino-2,3,4-trihydroxy-cyclohexyloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 118190-49-1 (5R,5aR,9S)-9-((1R,2R,3S,4R,5S)-5-Amino-2,3,4-trihydroxy-cyclohexyloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 118190-45-7 1L-(1,2,4,5/3)-2,3,4-tri-O-benzyl-1-O-p-toluenesulfonyl-1,2,3,4,5-cyclohexanepentol 
• 121513-05-1 (2R,3S,4R,5R)-2,3,4-Tris-benzyloxy-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone 

Relevant academic research and scientific papers

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).

FACILE CHEMO-ENZYMATIC SYNTHESES OF SELECTIVELY PROTECTED DERIVATIVES OF DEOXY-INOSITOLS

Selectively substituted symmetrical polyhydroxycyclohexanols like 3-deoxy-epi- (e.g. 2,4) and 1-deoxy-scyllo-inositol derivatives (e.g. 6) conveniently can be prepared by chemoenzymatic methods.

SYNTHESIS OF CARBOCYCLIC LIGNAN VARIANTS RELATED TO PODOPHYLLOTOXIN

Carbocyclic lignan variants related to podophyllotoxin were synthesized by a stereoselective BF3-catalyzed coupling of podophyllotoxin derivative with chiral aminocyclitols.