84170-91-2

Upstream product

• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 79386-70-2 Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester 
• 936220-96-1 (2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one 
• 82793-07-5 Benzoic acid (2R,3S,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester 
• 82793-06-4 Benzoic acid (2R,3S,4S,5S,6S)-5-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester 
• 84109-53-5 Benzoic acid (2S,3S,4R,5R,6S)-2-bromomethyl-5-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester 
• 84109-52-4 tert-Butyl-((2R,4aR,6S,7R,8R,8aS)-6-methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane 
• 84109-54-6 Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester 
• 84109-55-7 Benzoic acid (1R,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-vinyl-butyl ester 
• 84170-92-3 (2R,4aR,6S,7R,8S,8aS)-6-Methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 478944-12-6 Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester 
• 478944-09-1 Benzoic acid (1R,2S,3S)-3,4-dihydroxy-2-methyl-1-vinyl-butyl ester 
• 478944-11-5 Benzoic acid (R)-1-((R)-(S)-1-oxiranyl-ethyl)-allyl ester 

Relevant academic research and scientific papers

Synthesis and testing of 2alpha-modified 1alpha,25-dihydroxyvitamin D(3) analogues with a double side chain: marked cell differentiation activity.

The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D(3) were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity.

Synthesis of A-ring synthon of 2α-substituted vitamin d3 analogues utilizing Grignard reaction towards methyl 2,3-anhydro-4,6-o-benzylidene-α-D-manno-pyranoside

A concise route to the Trost A-ring precursor enyne for synthesizing 2α-substituted 1α,25-dihydroxyvitamin D3 (1) is described, in which the 2α-substituents could be introduced via addition reaction of Grignard reagent towards the sugar epoxide

REVISION OF THE ASSIGNMENT OF RELATIVE STEREOCHEMISTRY IN SIBIROSAMINE: SYNTHESIS OF METHYL N-TOSYL α-D-SIBIROSAMINOPYRANOSIDE

A synthesis of the N-toluenesulfonamide of α-methyl D-sibirosaminopyranoside has resulted in a reassignment of the relative stereochemistry of sibirosamine, a rare sugar found as its glycoside in sibiromycin.