857633-06-8

Upstream product

• 90-80-2 D-Glucono-1,5-lactone 
• 75-36-5 acetyl chloride 
• 111136-25-5 α-valienol 
• 1323271-55-1 C₁₈H₃₄O₁₀ 
• 1323271-65-3 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose 
• 1323271-61-9 C₁₉H₃₄O₉ 
• 1204745-32-3 (1S,2R,3S,4R)-5-acetoxymethyl-1-O-tert-butyldimethylsilyl-2,3-[(2R,3R)-2,3-dimethoxybutan-2,3-dioxy]-5-cyclohexene-1,2,3,4-tetraol 

Relevant academic research and scientific papers

The structure and stereochemistry of gabosine K: Syntheses of 7-O-acetylstreptol and 7-O-acetyl-1-epi-streptol

Gabosine K, whose structure was erroneously assigned previously as 7-O-acetyl-4-epi-streptol, has been synthesized for the first time from D-glucose via a key carbocyclization strategy, intramolecular direct aldol reaction of a 2,6-diketone, in 15 steps with 13.5% overall yield. In the same manner, (+)-7-O-acetyl-streptol has been constructed for NMR spectral comparison. The structure, relative and absolute configurations of (-)-gabosine K are now revised and established as (-)-7-O-acetyl-1-epi-streptol, that is, (1R,2S,3S,4R)-tetrahydroxy-5-acetoxymethy lcyclohex-5-ene. Since the specific rotation of the natural product is not available, the absolute configuration of natural gabosine K is either (-)-7-O-acetyl-1-epi-streptol or its enantiomer. Georg Thieme Verlag Stuttgart.

Short and efficient syntheses of gabosine I, streptol, 7-O-acetylstreptol, 1-epi-streptol, gabosine K, and carba α-d-glucose from δ-d-gluconolactone

δ-d-Gluconolactone was carbocyclized into an EOM-protected cyclohexenone in four steps involving perethoxymethylation, phosphonate anion addition, reduction, and oxidation with concomitant Horner-Wadsworth-Emmons alkenation. The stable key enone was effic