Study of the β-oxygen effect in the Barton-McCombie reaction for the total synthesis of (4R,5R)-4-hydroxy-γ-decalactone (Japanese orange fly lactone): a carbohydrate based approach was written by Desireddi, Janardana Reddi;Rao, Mora Mallikarjuna;Murahari, Kiran Kumar;Nimmareddy, Rajashekar Reddy;Mothe, Thirupathi;Lingala, Arun Kumar;Maiti, Bhimcharan;Manchal, Ravinder. And the article was included in RSC Advances in 2022.HPLC of Formula: 582-52-5 This article mentions the following:
Efficient and facile synthesis of Japanese orange fly lactone I was achieved from a com. available D-glucose by investigating Barton-McCombie reaction with furanose anomeric isomers (12α, β) with an overall yield of 12.6%. During course of this synthesis, β-oxygen effect was discovered in deoxygenation step at C-3 position using Barton-McCombie reaction, where substrate allows effect to operate in one of isomers but not in other. Under same reaction conditions, xanthate derived from β-furanose isomer afforded a high yield of deoxygenated product, whereas α-isomer produced a very low yield. The key transformations used were Wittig olefination, TEMPO mediated oxidation, and Barton-McCombie deoxygenation, resulting in a concise total synthesis of Japanese orange fly lactone I. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5HPLC of Formula: 582-52-5).
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF), or oxolane, is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.HPLC of Formula: 582-52-5
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem