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Crystal structure of 4-nitro ­ phenyl 6- O -ethyl- β - d -galacto ­ pyran ­ oside monohydrate

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ABSTRACT

The synthesis and crystal structure of the title compound, C14H19NO8·H2O, prepared in three steps from 6-O-ethyl-1,2;3,4-di-O-iso­propyl­idene-α-d-galacto­pyran­ose using protecting-group strategies employed in carbohydrate chemistry, is reported. The asymmetric unit consists of a single galactoside mol­ecule, in which the pyran­oid ring has a 4C1 conformation and the 4-nitro­phenyl moiety is essentially planar. In the crystal, each carbohydrate is surrounded by other d-galactose residues and water mol­ecules, linked by O—H⋯O hydrogen bonds involving all hy­droxy groups, giving a two-dimensional substructure lying parallel to (100) and extended into three dimensions by C—H⋯O inter­actions.

No MeSH data available.


Synthesis of the title compound (I): (i) AcCl, MeOH, HCl(aq), room temperature, closed system; (ii) 4-nitro­phenol, LiOH·H2O, acetone/H2O, room temperature; (iii) MeONa/MeOH, CH2Cl2, 273 K. The water mol­ecule of crystallization of (I) is not represented.
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fig4: Synthesis of the title compound (I): (i) AcCl, MeOH, HCl(aq), room temperature, closed system; (ii) 4-nitro­phenol, LiOH·H2O, acetone/H2O, room temperature; (iii) MeONa/MeOH, CH2Cl2, 273 K. The water mol­ecule of crystallization of (I) is not represented.

Mentions: The chemical synthesis of 4-nitro­phenyl 6-O-ethyl-β-d-galacto­pyran­oside monohydrate (I) was achieved in three steps, as shown in Fig. 4 ▸.


Crystal structure of 4-nitro ­ phenyl 6- O -ethyl- β - d -galacto ­ pyran ­ oside monohydrate
Synthesis of the title compound (I): (i) AcCl, MeOH, HCl(aq), room temperature, closed system; (ii) 4-nitro­phenol, LiOH·H2O, acetone/H2O, room temperature; (iii) MeONa/MeOH, CH2Cl2, 273 K. The water mol­ecule of crystallization of (I) is not represented.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
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getmorefigures.php?uid=PMC5382630&req=5

fig4: Synthesis of the title compound (I): (i) AcCl, MeOH, HCl(aq), room temperature, closed system; (ii) 4-nitro­phenol, LiOH·H2O, acetone/H2O, room temperature; (iii) MeONa/MeOH, CH2Cl2, 273 K. The water mol­ecule of crystallization of (I) is not represented.
Mentions: The chemical synthesis of 4-nitro­phenyl 6-O-ethyl-β-d-galacto­pyran­oside monohydrate (I) was achieved in three steps, as shown in Fig. 4 ▸.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The synthesis and crystal structure of the title compound, C14H19NO8·H2O, prepared in three steps from 6-O-ethyl-1,2;3,4-di-O-iso­propyl­idene-α-d-galacto­pyran­ose using protecting-group strategies employed in carbohydrate chemistry, is reported. The asymmetric unit consists of a single galactoside mol­ecule, in which the pyran­oid ring has a 4C1 conformation and the 4-nitro­phenyl moiety is essentially planar. In the crystal, each carbohydrate is surrounded by other d-galactose residues and water mol­ecules, linked by O—H⋯O hydrogen bonds involving all hy­droxy groups, giving a two-dimensional substructure lying parallel to (100) and extended into three dimensions by C—H⋯O inter­actions.

No MeSH data available.