51385-38-7

Upstream product

• 148657-22-1 methyl 2-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-3,4-dideoxy-α-D-hex-3-enopyranoside 

Downstream Products

• 73684-08-9 methyl 2,3,4-trideoxy-2,4-C-dimethyl-6-O-(p-toluenesulfonyl)-α-D-lyxo-hexopyranoside 
• 110561-00-7 ((2S,3R,6S)-5-Benzyloxy-6-methoxy-3-methyl-tetrahydro-pyran-2-yl)-methanol 
• 95015-45-5 methyl 2-O-benzyl-6-C-cyano-3,4,6-trideoxy-4-C-methyl-α-D-xylo(and lyxo)-hexopyranoside 
• 95015-46-6 ((2R,3R)-5-Benzyloxy-6-methoxy-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 110561-12-1 Trifluoro-methanesulfonic acid (2S,3R,6S)-5-benzyloxy-6-methoxy-3-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 110561-04-1 13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal 
• 80532-26-9 (2S,3S,6S)-3-Benzyloxy-6-(1-ethoxy-ethoxymethyl)-2-methoxy-3-methyl-tetrahydro-pyran 
• 604-70-6 2,3,4,6-tetra-O-acetyl-α-DL-altropyranoside 

Relevant academic research and scientific papers

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.