Methyl 6-deoxy-6-iodo-α-d-glucopyranoside: crystal structure and high-resolution NMR spectroscopy

Sikorski, Artur; Tuwalska, Dorota; Matjasik, Beata; Liberek, Beata

doi:10.1016/j.carres.2009.02.004

Cited by 3 publications

(4 citation statements)

References 27 publications

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“…For details of the synthesis, see Cheng et al (2011). For related structures, see Sikorski et al (2009), Robertson & Sheldrick (1965), Zhou et al (2002), Kurhade et al(2011). For the iodo derivative, see: Gulab et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

Methyl 6-azido-6-deoxy-α-D-galactoside

Cheng

Gulab²,

Timmer

et al. 2011

Acta Cryst E

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The structure of the title compound, C7H13N3O5, was solved using data from a multiple fragment crystal. The galactoside ring adopts a 4 C 1 chair conformation. In the crystal, the molecules are linked by strong O—H⋯O hydrogen bonds, which build linkages around the screw axis of the cell in a similar way to the iodo analogue. These C-5 and C-6 packing motifs expand to R 2 2(10), C 2 2(7) and C 2 2 2(8) motifs, as found in closely related compounds.

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Section: Related Literaturementioning

confidence: 99%

Methyl 6-azido-6-deoxy-α-D-galactoside

Cheng

Gulab²,

Timmer

et al. 2011

Acta Cryst E

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“…For the synthetic details, see Dangerfield et al (2009); Stocker et al(2010). For related structures, see Sikorski et al (2009), Robertson & Sheldrick (1965). For ring conformations see: Cremer & Pople (1975) and for hydrogen-bond motifs, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

“…1). The galactoside ring (C1-C5,O5) has a 1 C 4 chair conformation with Q 0.5902 (14) Å, θ & φ 3.36 15& 279 (2)° respectively (Cremer & Pople, 1975) similar to that of the corresponding glucopyranoside 0.563 5 Sikorski et al, 2009). The absolute configurations with C1(R), C2(R), C3(S), C4(R), C5(S) are consistent with that expected from the synthesis.…”

Section: S1 Commentmentioning

confidence: 99%

Methyl 6-deoxy-6-iodo-α-D-galactoside

Gulab¹,

Cheng

Timmer

et al. 2010

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 111 K; mean (C-C) = 0.002 Å; R factor = 0.021; wR factor = 0.050; data-to-parameter ratio = 33.3.In the crystal of the title compound, C 7 H 13 IO 5 , the molecules are linked by O-HÁ Á ÁO hydrogen bonds, which build linkages around one screw axis of the cell. These C(5) and C(6) packing motifs expand to R 2 2 (10) and C 2 2 (11) motifs and are similar to those found for closely related compounds. The galactoside ring has a 1 C 4 chair conformation. Related literature ExperimentalCrystal data

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“…Another triazole derivative, 5, analogue of 4c, was prepared by a similar method 20 from acetylated methyl--D-glucopyranoside with the azide group in position 6 (scheme 2). The final products were obtained in yields between 21% for 4c and 56% for 5.…”

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confidence: 99%

Synthesis of Novel Glycoconjugates Derived From Alkynyl Heterocycles through a Click Approach

Silva

Gonçalves

Oliveira‐Campos

et al. 2013

Synthetic Communications

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Abstract:The synthesis of a series of novel 1,4-disubstituted 1,2,3-triazole compounds bearing a D-glucose derivative and an heteroaromatic system is described. Alkylation of isatin, 3-methylcarbazole and one tetrahydro--carboline with propargyl bromide gave their N-propargyl derivatives in good yields. These compounds further reacted with acetylated D-glucose with the azide group in position 1, to give three final products and with peracetylated 6-azido-6-deoxyalpha-D-methylglucoside giving the corresponding derivative of tetrahydro--carboline.

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Methyl 6-deoxy-6-iodo-α-d-glucopyranoside: crystal structure and high-resolution NMR spectroscopy

Cited by 3 publications

References 27 publications

Methyl 6-azido-6-deoxy-α-D-galactoside

Methyl 6-azido-6-deoxy-α-D-galactoside

Methyl 6-deoxy-6-iodo-α-D-galactoside

Synthesis of Novel Glycoconjugates Derived From Alkynyl Heterocycles through a Click Approach

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