127446-62-2

Upstream product

• 148657-22-1 methyl 2-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-3,4-dideoxy-α-D-hex-3-enopyranoside 
• 58479-62-2 (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol 
• 148657-21-0 methyl 2-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-glucopyranoside 
• 127446-61-1 methyl 2-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-methylsulfonyl-α-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 21056-53-1 methyl O²-benzoyl-α-D-glucoside 

Downstream Products

• 148657-23-2 methyl 6-O-(tert-butyldiphenylsilyl)-2-O-(tributylstannylmethyl)-3,4-dideoxy-α-D-erythro-hex-3-enopyranoside 

Relevant academic research and scientific papers

The Still-Wittig rearrangement in the preparation of a synthetically useful 4C-hydroxymethyl-hex-2-enopyranoside

The Still-Wittig rearrangement of the stannyl-ether 9 is successfully carried out under optimal reaction conditions to give the 4C-hydroxymethyl-hex-2-enopyranoside 10 in good yields (70-74%).

En Route to Thromboxane Compounds from Carbohydrates, I. Synthesis of the Unsaturated Sugar Precursors

Allyl 4-C-hex-2-enopyranosides 18a-c, representing chiral precursors for the carbohydrate-based construction of the ring systems of thromboxane A2 and B2 were prepared by means of the Claisen-type rearrangement of the suitably substituted hex-3-enopyranosides 7a,b.The latter sugars were synthesized from allyl α-D-glucopyranoside (9) by modification of known procedures, including selective O-benzoylation with 1-(benzoyloxy)-1H-benzotriazole (11), and Tipson-Cohen sulfonyl ester elimination of the 3,4-di-O-mesylates 16 and 17.Studies on the corresponding methyl glycosides 8a-c showed a reduce d stability of the 6-O-(tert-butyldiphenylsilyl) ether group under the Tipson-Cohen reaction conditions.