A New Preparation of the Disaccharide β‐<scp>D</scp>‐ManNAcp‐(1 → 4)‐<scp>D</scp>‐Glc from Lactose Through a Highly Stereoselective β‐<scp>D</scp>‐Galpto β‐<scp>D</scp>‐ManNAcpTransformation

Attolino, Emanuele; Catelani, Giorgio; D’Andrea, Felicia; Nicolardi, Maria

doi:10.1081/car-200030011

Cited by 8 publications

(3 citation statements)

References 27 publications

(39 reference statements)

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“…Corresponding diols 11 and 13 were isolated in 80 and 74 % yields, respectively. For 6 and 8 , the acetal ring in 3′,4′ was also removed, thereby showing similar reactivity between the fused cycle and the one involving the primary position, and tetraol disaccharides 10 19a and 12 were again obtained with satisfactory yield (79 and 69 %, respectively).…”

Section: Resultsmentioning

confidence: 94%

“…MgSO 4 was used as the drying agent for solutions. Compound 4‐ O ‐(2‐acetamido‐6‐ O ‐benzyl‐3,4‐ O ‐isopropylidene‐2‐deoxy‐β‐ D ‐talopyranosyl)‐2,3:5,6‐di‐ O ‐isopro‐pylidene‐ aldehydo ‐ D ‐glucose dimethyl acetal ( 6 ),19a 4‐ O ‐(2‐acetamido‐2,6‐di‐ O ‐benzyl‐2‐deoxy‐β‐ D ‐mannopyranosyl)‐2,3:5,6‐di‐ O ‐isopropylidene‐ aldehydo ‐ D ‐glucose dimethyl acetal ( 7 ),19a 4‐ O ‐(2‐azido‐6‐ O ‐benzyl‐3,4‐ O ‐isopropylidene‐2‐deoxy‐β‐ D ‐galactopyranosyl)‐2,3:5,6‐di‐ O ‐isopropylidene‐ aldehydo ‐ D ‐glucose dimethyl acetal ( 8 ),19b 4‐ O ‐(2‐azido‐3,4,6‐tri‐ O ‐benzyl‐2‐deoxy‐β‐ D ‐glucopyranosyl)‐2,3:5,6‐di‐ O ‐isopropylidene‐ aldehydo ‐ D ‐glucose dimethyl acetal ( 9 )19c and 4‐ O ‐(2‐acetamido‐6‐ O ‐benzyl‐2‐deoxy‐β‐ D ‐talopyranosyl)‐2,3‐ O ‐isopropylidene‐ aldehydo ‐ D ‐glucose dimethyl acetal ( 10 )19a were prepared according to the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

“…4‐ O ‐(2‐Acetamido‐6‐ O ‐benzyl‐2‐deoxy‐β ‐ D ‐talopyranosyl)‐2,3‐ O ‐isopropylidene‐ D ‐ xylo ‐hexos‐5‐ulose Dimethyl Acetal (14): Regioselective oxidation of 10 19a (453.6 mg, 0.81 mmol) was performed according to the general procedure. The reaction was stopped after 1.5 h, purified with CHCl 3 then CHCl 3 /MeOH (9:1) to give pure 14 (300 mg, 67 %) as a clear syrup.…”

Section: Methodsmentioning

confidence: 99%

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Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

et al. 2014

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The synthesis of β‐D‐GlcNAc‐, β‐D‐GalNAc‐, β‐D‐ManNAc‐, and β‐D‐TalNAc‐(1→4)‐DNJ iminosugar disaccharides has been achieved, avoiding the glycosylation reaction, using a mixed tetracetonide of lactose [2,3:5,6:3′,4′‐tri‐O‐isopropylidene‐(6′‐O‐2‐methoxy‐2‐methylethyl)‐lactose dimethyl acetal] as starting material. The synthetic process is based on the transformation of the reducing unit of suitably protected β‐D‐hexosaminyl‐(1→4)‐aldehydo‐D‐glucose dimethyl acetal disaccharides into a deoxynojirimycin derivative. Key steps of the synthesis are: (a) the selective oxidation of the 5‐position of the D‐glucose unit, (b) release of the aldehydo function, (c) double reductive aminocyclisation of the 1,5‐dicarbonyl disaccharide intermediate, and (d) complete deprotection.

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Section: Resultsmentioning

confidence: 94%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

et al. 2014

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Chemical Valorization of Milk‐Derived Carbohydrates. Part 19. A New Preparation of the Disaccharide β‐D‐ManNAcp‐(1→4)‐D‐Glc from Lactose Through a Highly Stereoselective β‐D‐Galp to β‐D‐ManNAcp Transformation.

et al. 2005

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Regiospecific Synthesis of 4‐Deoxy‐D‐threo‐hex‐3‐enopyranosides by Simultaneous Activation–Elimination of the Talopyranoside Axial 4‐OH with the NaH/Im₂SO₂ System: Manifestation of the Stereoelectronic Effect

2006

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A new and high‐yielding method for the regioselective preparation of 4‐deoxy‐ and 2,4‐dideoxy‐2‐acetamido‐β‐D‐threo‐hex‐3‐enopyranosides has been developed. The process involves a simultaneous activation–elimination of the OH‐4 group of β‐D‐talopyranosides and 2‐acetamido‐2‐deoxy‐β‐D‐talopyranosides, mediated by the NaH/N,N′‐sulfuryldiimidazole system at –30 °C. The same reaction applied on the analogous β‐D‐galactopyranosides takes place without any regioselectivity, affording mixtures of hex‐3‐ and hex‐4‐enopyranosides. In the case of the methyl 2,3,6‐tri‐O‐benzyl‐α‐D‐talo‐ and α‐D‐galactopyranosides, the corresponding 4‐O‐imidazylates can be isolated by quenching the reactions at –30 °C. Upon warming these crude products to room temperature, the α‐talo‐4‐O‐imidazylate gives the corresponding hex‐3‐eno derivative in very high yield, but its α‐galacto analogue gives the hex‐4‐enopyranoside enol ether in poor yield. The different regiochemical outcome between the talo and the galacto series has been attributed to the stereoelectronic effect exerted, exclusively in talo‐configured compounds, by the axially disposed C‐2 electronegative substituent, which selectively accelerates the breaking of the antiperiplanar C(3)–H bond. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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A New Preparation of the Disaccharide β‐D‐ManNAcp‐(1 → 4)‐D‐Glc from Lactose Through a Highly Stereoselective β‐D‐Galpto β‐D‐ManNAcpTransformation

Cited by 8 publications

References 27 publications

Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

Chemical Valorization of Milk‐Derived Carbohydrates. Part 19. A New Preparation of the Disaccharide β‐D‐ManNAcp‐(1→4)‐D‐Glc from Lactose Through a Highly Stereoselective β‐D‐Galp to β‐D‐ManNAcp Transformation.

Regiospecific Synthesis of 4‐Deoxy‐D‐threo‐hex‐3‐enopyranosides by Simultaneous Activation–Elimination of the Talopyranoside Axial 4‐OH with the NaH/Im₂SO₂ System: Manifestation of the Stereoelectronic Effect

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A New Preparation of the Disaccharide β‐D‐ManNAcp‐(1 → 4)‐D‐Glc from Lactose Through a Highly Stereoselective β‐D‐Galpto β‐D‐ManNAcpTransformation

Cited by 8 publications

References 27 publications

Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

Chemical Valorization of Milk‐Derived Carbohydrates. Part 19. A New Preparation of the Disaccharide β‐D‐ManNAcp‐(1→4)‐D‐Glc from Lactose Through a Highly Stereoselective β‐D‐Galp to β‐D‐ManNAcp Transformation.

Regiospecific Synthesis of 4‐Deoxy‐D‐threo‐hex‐3‐enopyranosides by Simultaneous Activation–Elimination of the Talopyranoside Axial 4‐OH with the NaH/Im2SO2 System: Manifestation of the Stereoelectronic Effect

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Regiospecific Synthesis of 4‐Deoxy‐D‐threo‐hex‐3‐enopyranosides by Simultaneous Activation–Elimination of the Talopyranoside Axial 4‐OH with the NaH/Im₂SO₂ System: Manifestation of the Stereoelectronic Effect