1025446-75-6

Upstream product

• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 

Downstream Products

• 1025446-76-7 (2S,4R,6R)-1,2-O-isopropylidene-4-O-(4-methoxybenzyl)-6-O-benzyloct-7-yne-1,2,4,6-tetraol 
• 1206482-35-0 (2S,4S,6R)-1,2-O-isopropylidene-4-O-(4-nitrobenzoyl)-6-O-benzyloct-7-yne-1,2,4,6-tetraol 

Relevant academic research and scientific papers

A modular total synthesis of aculeatins A, B, E, F and 6-epi-aculeatins E, F

The total synthesis of aculeatins A, B, E and F confirming the assigned absolute configuration of recently isolated aculeatins E and F is documented. A convergent approach has been designed by the addition of both the terminal units (phenol and side chain) at an advanced stage. The central 1,3,5-triol unit with the requisite stereochemistry was prepared from the commercially available α-d-glucoheptonic-γ-lactone. Selective O-debenzylation during the hydrogenolysis of the diyne intermediate and the one pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total syntheses.

A carbohydrate-based approach for the total synthesis of aculeatin D and 6-epi-aculeatin D

(Chemical Equation Presented) A concise approach for the total synthesis of aculeatin D and 6-epi-aculeatin D employing differentially protected anti,anti-1,3,5-triol alkyne prepared from α-D-glucoheptonic-γ- lactone derivative is documented. Phenol protecting group manipulation for selective O-debenzylation during the hydrogenation of the diyne intermediate and one-pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total synthesis.