70632-46-1

Upstream product

• 70632-45-0 (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol 
• 39682-04-7 (3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid 
• 546-67-8 lead(IV) tetraacetate 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 

Downstream Products

• 121611-66-3 (3R,4S)-4-Benzyloxy-tetrahydro-furan-2,3-diol 
• 121701-09-5 (2S,3R)-2-benzyloxy-pent-4-ene-1,3-diol 
• 120417-92-7 (3aR,5S,6S,6aR)-5-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 89755-56-6 <3aR(3aα,5β,6β,6aα)>-tetrahydro-2,2-dimethyl-5-(2-propen-1-yl)-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole 
• 76768-64-4 (3aR,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole 

Relevant academic research and scientific papers

Total synthesis of (+)-mupirocin H from d-glucose

Enantioselective total synthesis of mupirocin H is accomplished starting from d-glucose featuring strategic application of d-glucose derived chirality, diastereoselective Still-Barrish hydroboration, and further elaboration of carbon chain to furnish a phenyltetrazolyl sulfone intermediate, which on coupling with (2S,3S)-2-methyl-3-(triisopropylsilyloxy)butanal under Julia-Kocienski olefination conditions gave an advanced E-olefinic intermediate selectively. The E-olefin was transformed to the 4-hydroxynitrile, a prefinal substrate, which on acid-catalyzed oxidative lactonization furnished the target molecule mupirocin H in 19 steps from known compound 6 (longest linear sequence) with an overall yield of 4.96%.

NOVEL SYNTHETIC EQUIVALENTS OF DIFFERENTIALLY PROTECTED TARTARIC ALDEHYDES. A SIMPLE ROUTE TO USEFUL C-4 CHIRAL SYNTHONS.

The synthesis of 4-acetoxy-3-O-benzyl-1,2-O-isopropylidene aldotetroses from D-glucose is reported.These synthetic equivalents of tartaric aldehydes are chemoselectively reduced at the acetoxylated center leading to a series of useful differentially protected C-4 chiral synthons.