61773-60-2

Upstream product

• 125472-23-3 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-sulfonyl-α-D-erythro-hex-2-enopyranoside 
• 108-93-0 cyclohexanol 
• 2873-29-2 D-glucal triacetate 

Relevant academic research and scientific papers

A mild, efficient and α-selective glycosidation by using potassium dodecatungstocobaltate trihydrate as catalyst

Treatment of tri-O-acetyl-D-glucal3,4,6-Tri-O-acetyl-1,5-anhyro-2-deoxy-D- arabinahex-1-enitol.1 1 with several alcohols in the presence of catalytic amount of POM (K5CoW12O40· 3H2O) as a heterogeneous, reusable, efficient and environmentally benign catalyst under neutral conditions and ambient temperature gave the corresponding 2,3-unsaturated glycopyranosides in excellent yields, with good anomeric selectivity. This catalyst proved to be not efficient for phenols.

Amberlyst 15-catalyzed efficient synthesis of 2,3-unsaturated glycosides via Ferrier rearrangement for glycal

Amberlyst 15 serves as an inexpensive, effective, and environmentally friendly catalyst in converting 3,4,6-tri-O-acetyl-D-glucal (1) into 2,3-unsaturated O- and S-glycosides via Ferrier rearrangement in moderate to excellent yields with high α selectivity. Copyright Taylor & Francis Group, LLC.

Reactions of various nucleophiles with d-glucal over keggin-type heteropoly compounds: A simple, rapid, and expedient method for the synthesis of pseudoglycals

The reaction of benzyl alcohol with 3,4,6-tri-O-acetyl-d-glucal has been investigated with several heteropoly compounds, and the optimal catalyst is 12-tungstophosphoric acid supported on carbon. In the presence of this catalyst, various alcohols gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields and good anomeric selectivity under solvent-free condition. 4,6-Di-O-acetyl-2,3-dideoxy - d-erythro-hex-2- enopyranosyl cyanide and ethyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio - d-erythro-hex-2-enopyranoside have also been prepared with trimethylsilyl cyanide and ethanthiol as nucleophiles, respectively. The catalyst could be easily recovered and reused several times with slight loss of activity. The selectivity to give α-anomers predominantly did not show any change in all runs.

Bi(OTf)3 and SiO2-Bi(OTf)3 as effective catalysts for the ferrier rearrangement

Bi(OTf)3 and SiO2-Bi(OTf)3 are found to effectively catalyze the Ferrier rearrangement of tri-O-acetyl glycals with different alcohols providing an effective route to 2,3-imsaturated O-glycosides with good anomeric selectivity and good to excellent yields after short reaction times.

Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals

Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good α selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.

Lithium tetrafluoborate catalyzed ferrier rearrangement - Facile synthesis of alkyl 2,3-unsaturated glycopyranosides

Treatment of tri-O acetyl-D-galactal 1 and tri-O-acetyl-D-glucal 2 with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl, 2,3- unsaturated glycopyranosides 3-18 (50-86%).

Use of 2-phenylsulphonyl cyclic ethers in the preparation of tetrahydropyran and tetrahydrofuran acetals and in some glycosidation reactions

2-Phenylsulphonyl cyclic ethers undergo facile displacement of the sulphonyl group by alcohols, in the presence of magnesium bromide etherate and sodium bicarbonate in tetrahydrofuran, to give goodyields of the corresponding acetals.