213337-95-2

Upstream product

• 1045730-81-1 C₃₅H₃₆O₅ 
• 214041-43-7 (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal 
• 78136-16-0 2,3,4,6-tetra-O-benzyl-D-glucitol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 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 

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 
• 213338-01-3 [3S-(3α,4β,5α)]-1-(acetoxymethyl)-3,4,5-tris(benzyloxy)-1-cyclopentene 

Relevant academic research and scientific papers

Synthesis of an Orthogonally Protected Polyhydroxylated Cyclopentene from l-Sorbose

The use of l-sorbose in the synthesis of functionalized cyclopentene derivatives was accomplished. These cyclopentene derivatives are related to those found in naturally occurring jatrophane frameworks and in other bioactive compounds. The formation of allyl α-l-sorbopyranoside was a key synthetic step. Regioselective introduction of protecting groups was followed by the hydrolysis of the allyl glycoside to furnish a fully protected acyclic l-sorbose derivative. This acyclic intermediate was subsequently used to give an orthogonally protected polyhydroxylated cyclopentene, which has potential for further synthesis of bioactive compounds. The protected cyclopentene itself showed a clear cytotoxic activity when tested against a panel of human cancer cell lines (HT29, LS174T, SW620, A549, and HeLa cells).

The synthesis of polyoxygenated, enantiopure cyclopentene derivatives using the Ramberg-B?cklund rearrangement

A novel approach to polyoxygenated enantiopure cyclopentenes, α-chlorocyclopentenones and cyclopentenones is described which utilizes the Ramberg-Ba?cklund rearrangement of thiosugar-derived sulfones. A formal synthesis of the natural aminocyclopentitol, trehazolamine is also reported.

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.