2012
DOI: 10.1016/j.tetlet.2012.04.039
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Mild acetal cleavage using B-chlorocatecholborane in the synthesis of rearrangement-sensitive 2-arachidonoylglycerol

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Cited by 5 publications
(5 citation statements)
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“…Upon omitting the silane, we observed a partial cleavage of the 4,6-O-benzylidene moiety (Table 3, entry 5), presumably resulting from nucleophilic attack of chloride on the PhBCl 2 -activated acetal, as already observed with Bchlorocatecholborane. 78 This last experiment established that it is important to add Et 3 SiH prior to PhBCl 2 to avoid such side reaction. Taken together, these results confirm that, when using the PhBCl 2 /Et 3 SiH reagent system in CH 2 Cl 2 , the kinetics of the reductive opening reaction is much faster than both the chlorosilane reduction/hydroboration cascade and 4,6-O-benzylidene cleavage.…”
Section: ■ Results and Discussionmentioning
confidence: 98%
See 1 more Smart Citation
“…Upon omitting the silane, we observed a partial cleavage of the 4,6-O-benzylidene moiety (Table 3, entry 5), presumably resulting from nucleophilic attack of chloride on the PhBCl 2 -activated acetal, as already observed with Bchlorocatecholborane. 78 This last experiment established that it is important to add Et 3 SiH prior to PhBCl 2 to avoid such side reaction. Taken together, these results confirm that, when using the PhBCl 2 /Et 3 SiH reagent system in CH 2 Cl 2 , the kinetics of the reductive opening reaction is much faster than both the chlorosilane reduction/hydroboration cascade and 4,6-O-benzylidene cleavage.…”
Section: ■ Results and Discussionmentioning
confidence: 98%
“…To further explore the minimum requirements for the reaction, we decreased the amount of PhBCl 2 to 1.1 equiv; however, the reaction did not proceed to completion, and we recovered 43% of starting material 1 along with 54% of compound 3a (Table , entry 4). Upon omitting the silane, we observed a partial cleavage of the 4,6- O -benzylidene moiety (Table , entry 5), presumably resulting from nucleophilic attack of chloride on the PhBCl 2 -activated acetal, as already observed with B-chlorocatecholborane . This last experiment established that it is important to add Et 3 SiH prior to PhBCl 2 to avoid such side reaction.…”
Section: Resultsmentioning
confidence: 99%
“…To date, 2-AG is synthesized by either chemical [16][17][18][19] or chemoenzymatic methods To date, 2-AG is synthesized by either chemical [16][17][18][19] or chemoenzymatic methods [20][21][22][23]. The chemical methods described for the synthesis of 2-AG are based on the same procedure: acylation of suitable 1,3-protected glycerol, or glycidol, precursors with an activated arachidonic acid derivative, followed by deprotection and separation of the isomeric arachidonoylglycerols.…”
Section: -Arachidonoylglycerol (2-agmentioning
confidence: 99%
“…B-Chlorocatecholborane was also used for acetal cleavage of cis-arachidonoylbenzylidene glycerol [19] that demonstrated the mildness of the reagent on an especially sensitive transformation while also affording an improved quality of product of current interest. Nevertheless, the silyl [24] and benzyl [17,19] protected glycerol approaches experienced at least 5% rearrangement, demonstrating the sensitivity of this molecule to deblocking conditions and identifying it as a probe of the mildness of reaction conditions.…”
Section: -Arachidonoylglycerol (2-agmentioning
confidence: 99%
“…Although some researchers have successfully synthesized pure 2-AG by chemical methods (Roche et al, 2012;Cartoni et al, 2004), 2-AG is extremely unstable. The ratio of 1-AG and 2-AG at equilibrium state is 9:1 (Andrews et al, 2008).…”
Section: Introductionmentioning
confidence: 99%