The acetonation of lactose and benzyl β-lactoside with 2-methoxypropene

Alonso-Lopez, M.; Barbat, Joēlle; Fanton, Elizabeth; Fernández‐Mayoralas, Alfonso; Gelas, Jacques; Horton, Derek; Martín‐Lomas, Manuel; Penadés, Soledad

doi:10.1016/s0040-4020(01)90057-2

Cited by 22 publications

(2 citation statements)

References 17 publications

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“…A second 18-crown-6 ether moiety was built onto the lactoside unit of 651 by hydrolysis of the acetonide protecting group and reaction with pentaethylene glycol ditosylate to give 652 . Taking advantage of a one pot procedure involving kinetic acetonation of 645 with 2-methoxypropene, benzylation and mild acid hydrolysis, the 6,6′-dihydroxy derivatives 646 was prepared with a 42% yield and then reacted with tetraethylene glycol ditosylate to afford 649 [ 270 ].…”

Section: Phase-transfer Catalystsmentioning

confidence: 99%

Synthesis and Applications of Carbohydrate-Based Organocatalysts

et al. 2021

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Organocatalysis is a very useful tool for the asymmetric synthesis of biologically or pharmacologically active compounds because it avoids the use of noxious metals, which are difficult to eliminate from the target products. Moreover, in many cases, the organocatalysed reactions can be performed in benign solvents and do not require anhydrous conditions. It is well-known that most of the above-mentioned reactions are promoted by a simple aminoacid, l-proline, or, to a lesser extent, by the more complex cinchona alkaloids. However, during the past three decades, other enantiopure natural compounds, the carbohydrates, have been employed as organocatalysts. In the present exhaustive review, the detailed preparation of all the sugar-based organocatalysts as well as their catalytic properties are described.

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Section: Phase-transfer Catalystsmentioning

confidence: 99%

Synthesis and Applications of Carbohydrate-Based Organocatalysts

et al. 2021

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“…Penades and Martin-Lomas [72][73][74] prepared such derivatives by reaction of the corresponding ditosylates with appropriately protected derivatives of benzyllactoside (Scheme 22 and 23).…”

Section: Receptors Containing Disaccharide Unit In the Structurementioning

confidence: 99%

Sugar Derived Crown Ethers and Their Analogs: Synthesis and Properties

Jarosz¹,

Listkowski

2006

COC

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ChemInform Abstract: Acetonation of Lactose and Benzyl β‐Lactoside with 2‐Methoxypropene.

et al. 1987

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321ChemInform Abstract Acetonation of lactose (I) with excess 2-methoxypropene (II) under the conditions indicated in the scheme yields two products which are acetylated and isolated as the anomeric mixtures (III) and (IV) (no yields given). 1H NMR data reveal that the diacetal formed in this reaction has structure (III) and not, as previously reported, structure (V). Furthermore, the reaction method is investigated forsome lactosides, especially for benzyl lactoside. In all cases, retention of the interglycosidic linkage is observed. In order to test the synthetic utility of kinetic acetonation, the chiral macrocyclic ether (VIII) is prepared in a one-pot procedure from the lactoside (VI).

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The acetonation of lactose and benzyl β-lactoside with 2-methoxypropene

Cited by 22 publications

References 17 publications

Synthesis and Applications of Carbohydrate-Based Organocatalysts

Synthesis and Applications of Carbohydrate-Based Organocatalysts

Sugar Derived Crown Ethers and Their Analogs: Synthesis and Properties

ChemInform Abstract: Acetonation of Lactose and Benzyl β‐Lactoside with 2‐Methoxypropene.

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