288584-96-3

Upstream product

• 288585-01-3 phenyl 2-O-(allyl(dimethyl)silyl)-3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 161275-25-8 3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene 
• 1015481-45-4 ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1011723-04-8 glucal epoxide 
• 128775-56-4 phenyl 3,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 

Downstream Products

• 1037204-41-3 C₄₆H₅₄O₆Si 
• 440362-96-9 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester 
• 797010-94-7 Methanesulfonic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-pyran-3-yl ester 
• 797010-96-9 Methanesulfonic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester 
• 797010-98-1 (2R,3R,4R,4aR,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran 
• 320576-38-3 (2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol 

Relevant academic research and scientific papers

1,5-Hydrogen Atom Transfer/Surzur-Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems

The 1,5-HAT-1,2-(ester)alkyl radical migration (Surzur-Tanner rearrangement) radical/polar sequence triggered by alkoxyl radicals has been studied on a series of C-glycosyl substrates with 3-C-(α,β-d,l-glycopyranosyl)1-propanol and C-(α-d,l-glycopyranosyl)methanol structures prepared from chiral pool d- and l-sugar. The use of acetoxy and diphenoxyphosphatoxy as leaving groups provides an efficient construction of 10-deoxy-1,6-dioxaspiro[4.5]decane and 4-deoxy-6,8-dioxabicyclo[3.2.1]octane frameworks. The alkoxyl radicals were generated by the reaction of the corresponding N-alkoxyphthalimides with group 14 hydrides [n-Bu3SnH(D) and (TMS)3SiH], and in comparative terms, the reaction was also initiated by visible light photocatalysis using the Hantzsch ester/fac-Ir(ppy)3 procedure. Special attention was devoted to the influence of the relative stereochemistry of the centers involved in the radical sequence on the reaction outcome. The addition of BF3?Et2O as a catalyst to the radical sequence resulted in a significant increase in the yields of the desired bicyclic ketals.

A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.

Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI50 values) below 10 μM, the C-gluco

Synthesis of 4,8-anhydro-d-glycero-d-ido-nonanitol 1,6,7-trisphosphate as a novel IP3 receptor ligand using a stereoselective radical cyclization reaction based on a conformational restriction strategy

4,8-Anhydro-d-glycero-d-ido-nonanitol 1,6,7-trisphosphate (9), designed as a novel IP3 receptor ligand having an α-C-glycosidic structure, was synthesized via a radical cyclization reaction with a temporary connecting allylsilyl group as the ke

Diisobutylaluminium hydride (DIBAL-H) as a molecular scalpel: A new mechanistic proposal for a spiroketal rearrangement

Taking advantage of our knowledge of the capacity of DIBAL-H to de-O-alkylate, we propose an alternative mechanism for a spiroketal rearrangement described by E. Suàrez. We also show that this proposal can account for the formation of the secondary product, whose original structure we propose to correct.

Stereoselective synthesis of α- and β-C-glucosides via radical cyclization with an allylsilyl tether. Control of the stereoselectivity by changing the conformation of the pyranose ring

An efficient method for preparing both 1α- and 1β-C-glucosides having a 3-hydroxypropyl group at the anomeric position via a radical cyclization reaction with an allylsilyl tether was developed. The stereoselectivity of the radical cyclization can be cont