213338-01-3

Upstream product

• 78136-16-0 2,3,4,6-tetra-O-benzyl-D-glucitol 
• 213337-93-0 (3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione 
• 213337-91-8 (3aR,4S,5R,6R,6aS)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione 
• 214041-43-7 (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 213337-99-6 Acetic acid (3aS,4S,5R,6R,6aR)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester 
• 213337-97-4 Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester 
• 108-24-7 acetic anhydride 
• 213337-95-2 ((((1S,2R,3R)-4-((benzyloxy)methyl)cyclopent-4-ene-1,2,3-triyl)tris(oxy))tris(methylene))tribenzene 

Downstream Products

• 213338-04-6 [3S-(3α,4β,5α)]-3,4,5-tris(benzyloxy)-1-(hydroxymethyl)-1-cyclopentene 
• 213338-06-8 [1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane 
• 213338-08-0 [1S-(1α,2β,3α,4β,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane 
• 213338-10-4 [1R-(1α,2β,3α,4β,5β)]-5-azido-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-1-cyclopentanol 
• 213338-12-6 [1S-(1α,2α,3β,4α,5β)]-5-azido-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-1-cyclopentanol 

Relevant academic research and scientific papers

A Highly Efficient Pinacol Coupling Approach to Trehazolamine Starting from D-Glucose

A short and very efficient synthesis of trehazolamine (3), the aglycon of the potent trehalase inhibitor trehazolin (2), has been achieved starting from D-glucose. The key transformation in this approach is a high-yielding two-step, one-pot sequence consisting of a Swern oxidation of a 1,5-diol followed by a reductive carbocyclization of the resultant 1,5-dicarbonyl compound promoted by samarium diiodide. The overall yield of 3 is 39% over nine steps from 2,3,4,6-tetra-O-benzyl-D-glucose (5). An even shorter synthesis of 30, a diastereoisomeric analogue of 3, is also described starting from 5. The key transformation in this second route is a highly stereoselective ketone oxime ether reductive carbocyclization promoted also by samarium diiodide. The overall yield of 30 is 57% over four steps from 5.