506423-00-3

Upstream product

• 2873-29-2 D-glucal triacetate 
• 67-56-1 methanol 
• 58871-10-6 3,4-di-O-benzyl-D-glucal 
• 13265-84-4 D-glucal 
• 129840-37-5 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol 
• 58871-09-3 6-O-tert-butyldimethylsilyl-D-glucal 

Downstream Products

• 506423-02-5 C₂₁H₂₅IO₄ 
• 175844-98-1 methyl 3,4-di-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 

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.

Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides

The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (α or β, respectively).