141404-08-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 95639-53-5 3(R),5(R)-trihydroxycyclohexanone 
• 141404-07-1 (3R,5R)-3,5-bis[tert-butyl(dimethyl)silyloxy]-1-(hydroxymethyl)-1,4-cyclohexanediol 
• 506423-07-0 (1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol 
• 506423-05-8 (2S,3R,5R)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone 
• 506423-10-5 (3R,5R)-3,4,5-Tris-benzyloxy-cyclohexanol 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 
• 189758-77-8 methyl 3,4-di-O-benzyl-2-deoxy-5-methylene-α-D-xylopyranoside 
• 725268-38-2 (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone 
• 175844-98-1 methyl 3,4-di-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 
• 81308-73-8 (3R,5R)-3,4,5-Tris-benzyloxy-cyclohexanone 
• 119943-96-3 Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside 
• 145149-85-5 Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside 

Downstream Products

• 141404-09-3 (3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone 
• 376353-72-9 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione 
• 159685-66-2 <(aS^*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-<(trimethylsilyl)oxy>cyclohexylidene>acetic acid methyl ester 
• 159685-66-2 <(aR^*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-<(trimethylsilyl)oxy>cyclohexylidene>acetic acid methyl ester 
• 160399-72-4 <(aS^*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-hydroxycyclohexylidene>acetic acid methyl ester 
• 160399-72-4 <(aR^*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-hydroxycyclohexylidene>acetic acid methyl ester 

Relevant academic research and scientific papers

2-Methylene 19-nor-25-dehydro-1α-hydroxyvitamin D3 26,23-lactones: Synthesis, biological activities and molecular basis of passive antagonism

To investigate the molecular mechanism of vitamin D receptor (VDR) antagonists having no structurally bulky group interfering with helix 12 of the ligand-binding domain of the VDR, we have synthesized four diastereomers at C(20) and C(23) of 19-nor-1α-hydroxyvitamin D3 25-methylene-26,23-lactone bearing a 2MD-type A-ring. All four analogs showed significant VDR affinity. Transactivation was tested by using Cos7 cells and HEK293 cells. In both types of cells, LAC67a showed little transactivation potency and inhibited the activation induced by the natural hormone concentration-dependently, indicating that LAC67a works as an antagonist for the VDR in these cells. LAC67b, LAC82a and LAC82b similarly acted as VDR antagonists in Cos7 cells, but in HEK293 cells they behaved as potent VDR agonists. Docking of four lactones into the VDR-LBD, followed by structural analysis, demonstrated that each lactone lacks the hydrophobic interaction with helix12 necessary for maintaining the active conformation of the VDR, indicating that these lactones are passive-type antagonists. Furthermore, each docking structure explained the characteristic transactivation profiles of the four lactones. On the basis of our present findings, we suggest that the ligand acts as an agonist if there are appropriate coactivators in the cells to bind to the looser VDR-ligand complex, and as an antagonist if there are no such appropriate coactivators. The molecular basis of the passive antagonism is discussed in detail.

Synthesis of a-ring synthon of 19-nor-1alpha,25-dihydroxyvitamin D3 from (D)-glucose

The present invention provides a method for the synthesis of an A-ring synthon phosphine oxide used in the preparation of 19-nor vitamin D compounds, and to novel synthetic intermediates formed during the synthesis. The new method prepares the phosphine oxide from (D)-glucose.

Novel synthesis of 2-substituted 19-norvitamin D A-ring phosphine oxide from D-glucose as a building block

19-Norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from D-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall yield by this novel cost-effective method.

19-Nor-vitamin D3 compounds with substitutent at 2-position

The 2α and 2β-hydroxy as well as the 2α(3'-hydroxypropoxy)- and 2β(3'-hydroxypropoxy)- and 2α(benzyloxy)- analogs of 19-nor-1α,25-dihydroxyvitamin D3 are disclosed. The two 2-hydroxy analogs showed in vivo calcium transport with little or no bo