<scp>l</scp>-Fucose from Vitamin C with Only Acetonide Protection

Liu, Zilei; Yoshihara, Akihide; Wormald, Mark R.; Jenkinson, Sarah F.; Gibson, Vicky; Izumori, Ken; Fleet, George W. J.

doi:10.1021/ol502733x

Cited by 9 publications

(7 citation statements)

References 51 publications

(7 reference statements)

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“…Many iminosugar syntheses start from monosaccharide starting materials (Wood et al, 2018;Lee et al, 2012;Rasmussen & Jensen, 2011). Reducing the number of protecting groups and removing the need for purification by chromatography are useful strategies to a more expedited synthesis of analogues (Katritzky et al, 1991;Liu et al, 2014).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

et al. 2020

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Short syntheses to high Fsp 3 index natural-product analogues such as iminosugars are of paramount importance in the investigation of their biological activities and reducing the use of protecting groups is an advantageous synthetic strategy. An isopropylidene group was employed towards the synthesis of seven-membered ring iminosugars and the title compound, C9H15N3O5, was crystallized as an intermediate, in which the THF ring is twisted and the dioxolane ring adopts an envelope conformation: the dihedral angle between the rings is 67.50 (13)°. In the crystal, the hydroxyl groups participate in O—H...(O,O) and O—H...N hydrogen-bonding interactions, which generate chains of molecules propagating parallel to the a-axis direction. There is a notable non-classical C—H...O hydrogen bond, which cross-links the [100] chains into (001) sheets.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

et al. 2020

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“…It should be noted that Szostak and co-authors reported a similar reaction with the use of Piv 2 O as an activating reagent during the submission. [18] Compared with our catalytic system, the reaction was conducted at a higher temperature (160°C) and seemed to be only applicable to H-phosphonates and Ph 2 PH. Scheme 2.…”

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“…(Boc) 2 O, 2.0 equiv. base was heated in 1 mL of solvent at the indicated temperature for18 h. [b] 31 P NMR yield using methyldiphenylphine oxide as an internal standard. [c] 5 mol-% Pd 2 (dba) 3 .…”

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Palladium-Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)-H Compounds

2020

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A direct decarbonylative phosphorylation of benzoic acids catalyzed by palladium was disclosed. Under the reaction conditions, a wide range of benzoic acids coupled readily with all the three kinds of P(O)–H compounds, i.e. secondary phosphine oxides, H‐phosphinates and H‐phosphonates, producing the corresponding organophosphorus compounds in good to high yields. This reaction could be conducted at a gram scale and applied in the late‐stage phosphorylative modification of carboxylic acids drug molecules. These results well demonstrated the potential synthetic value of this new reaction in organic synthesis.

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“…Heptonic acid lactones with only acetonide protection derived from Kiliani synthesis on aldoses or ketoses are well-established intermediates for the efficient synthesis of highly functionalized targets . This paper underlines the value of triacetonides derived from seven carbon sugars; 2 is a divergent intermediate for access to rare sugars possessing either a d -gulo or l -gluco structural motif with any oxidation level at C1 or C6. This approach, which may be general for heptonates, increases chemical and biotechnological procedures for easy access to rare sugars …”

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Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d-Gulose, 6-Deoxy-d-gulose, l-Glucose, 6-Deoxy-l-glucose, and Related Sugars

et al. 2016

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Ease of separation of petrol-soluble acetonides derived from the triacetonide of methyl glucoheptonate allows scalable syntheses of rare sugars containing the l-gluco or d-gulo structural motif with any oxidation level at the C6 or C1 position of the hexose, usually without chromatography: meso-d-glycero-d-guloheptitol available in two steps is an ideal entry point for the study of the biotechnological production of heptoses.

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l-Fucose from Vitamin C with Only Acetonide Protection

Cited by 9 publications

References 51 publications

Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

Palladium-Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)-H Compounds

Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d-Gulose, 6-Deoxy-d-gulose, l-Glucose, 6-Deoxy-l-glucose, and Related Sugars

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