175844-98-1

Upstream product

• 145149-85-5 Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside 
• 1184705-42-7 methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside 
• 1184705-45-0 methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside 
• 1184705-48-3 methyl 3,4-di-O-benzyl-2-deoxy-6-O-trityl-α-D-glucopyranoside 
• 214068-17-4 methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 506423-00-3 methyl 3,4-di-O-benzyl-2-deoxy-β-D-arabino-hexopyraboside 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 
• 119943-96-3 Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 6087-40-7 (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran 

Downstream Products

• 189758-77-8 methyl 3,4-di-O-benzyl-2-deoxy-5-methylene-α-D-xylopyranoside 
• 1184705-68-7 (3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene 
• 1184705-74-5 (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone 
• 1184705-70-1 (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone 
• 1184705-79-0 (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene 
• 1184705-82-5 (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene 
• 1184705-76-7 (3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene 

Relevant academic research and scientific papers

Synthesis of calystegine A3 from glucose by the use of ring-closing metathesis

A synthesis of the nortropane alkaloid calystegine A3 is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine and allylated in the same pot. The functionalized nona-l,8-diene, thus obtained, is converted into the sevenmembered carbon skeleton in calystegine A3 by ring-closing olefin metathesis. Subsequent deoxygenation by the BartonMcCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A3. The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.

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.