81308-73-8

Upstream product

• 81319-65-5 C₂₇H₂₉NO₅ 
• 81319-65-5 C₂₇H₂₉NO₅ 
• 189758-77-8 methyl 3,4-di-O-benzyl-2-deoxy-5-methylene-α-D-xylopyranoside 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 
• 81308-68-1 Acetic acid (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl ester 
• 507232-65-7 C₂₇H₃₀O₄ 
• 81319-64-4 Acetic acid (4R,6R)-3-acetoxy-4,5,6-tris-benzyloxy-2-nitro-cyclohexyl ester 
• 81319-63-3 (4R,6R)-4,5,6-Tris-benzyloxy-2-nitro-cyclohexane-1,3-diol 
• 506423-09-2 tert-Butyl-dimethyl-((3R,5R)-3,4,5-tris-benzyloxy-cyclohexyloxy)-silane 
• 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 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 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 

Downstream Products

• 141404-09-3 (3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone 
• 141404-08-2 (3R,5R)-3,5-bis[tert-butyl(dimethyl)silyloxy]-4-hydroxycyclohexanone 
• 95639-53-5 3(R),5(R)-trihydroxycyclohexanone 

Relevant academic research and scientific papers

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.

REDUCTIVE ONE-STEP ELIMINATION OF AN ACETOXYL RESIDUE AT β-POSITION OF A NITRO GROUP: SYNTHESES OF (-)-SHIKIMIC ACID FROM D-MANNOSE AND 2-DEOXYSTREPTAMINE PENTAACETATE FROM N-ACETYL-D-GLUCOSAMINE

By utilizing a reductive one-step elimination reaction of an acetoxyl residue at β-position of the nitro group in cyclitols, a synthesis of the ketocyclitol triacetate (15a), which was already converted to (-)-shikimic acid (16) and (-)-guinic acid (17), from D-mannose (4) and a conversion from N-acetyl-D-glucosamine (18) to 2-deoxystreptamine pentaacetate (22) have been accomplished.