Glycosides methyl 2-deoxy

Me glycoside Methyl 2-deoxy-2-fluoro-a-D-arabinofuranoside C6H11FO4 166.149 Syrup. [a]g -1-141 (c, 0.7 in EtOH). 

Me glycoside Methyl 2-deoxy-2-fluoro-D-ribofuranoside C6H11FO4 166.149 Cryst. (EtOAc/petrol). Mp 81-83°. 

Me glycoside Methyl 2-deoxy-a-D-erythm-pentopyranoside C6H12O4 148.158 Mp 95°. [a]g +40.1 (H2O). 

The key intermediate 14, a stable tetrasubstituted tetrahydropyran derivative, was obtained from commercially available methyl o-glucopyranoside 12 via a three-step reaction sequence (Scheme 4). First the primary hydroxyl group was protected as thexyldimethylsilyl (TDS) ether, then the other OH groups were methylated under standard conditions to give 13. The latter glycoside was deoxy-genated at the anomeric position by treatment at room temperature with a Lewis acid (trimethylsilyl triflate) and a hydride donor (triethylsilane). This treatment also... 

Unsubstituted acetals and methyl glycosides of deoxy sugars have also been investigated by mass spectrometry.2498 357 It is possible to differentiate between 3-, 5-, and 6-deoxy-l, 2-O-isopropylidenehexofuranoses from their mass spectra. The differences in the mass spectra of methyl 3- and 4-deoxy-pentopyranosides are also sufficient for their characterization. In the spectra of 2- and 3-deoxypentofuranosides, however, the differences reside in the relative intensities of certain peaks and do not allow definitive distinctions. 

Table 3.5 Relative rates of hydrolysis k/liQ of methyl deoxy-a-D-pyranosides relative to that of the parent sugar (see Fig. 3.7) (ko is the rate constant for the hydrolysis of parent glycoside under the same conditions)...

Me glycoside Methyl 4-amino-4-deoxy-a-D-arabinopyranoside C H,3N04 M 163.173... 

Me glycoside Methyl 3-amino-3-deoxy-a-D-allopyranoside C7H15NO5 193.199 Extremely hygroscopic cryst. (EtOH/ Et20) (as hydrochloride). [a]o -1-103.3 (c, 2 in D2O). 

Me glycoside Methyl S-amino-S-deoxy-fS-D-allopyranoside C7H15NO5 193.199 Mp 199-200°. 

Me glycoside Methyl 2-amino-2-deoxy-P-D-arabinopyranoside C6H13NO4 163.173 Solid by subl. Mp 135° (crude). [a]g -226 (c, 1.02 in H2O). 

Me glycoside Methyl 4-amino-4-deoxy-a-D-arabinopyremoside C6H13NO4 163.173 Cryst. (EtOH) (as hydrochloride). Mp 180-183° (hydrochloride), [ajo +3 (c, 1.75 in H2O). 

Me glycoside Methyl 6-amino-6-deoxy-x-L-idopyranoside C7H15NO5 193.199 Solid + V2 H2CO3. Md -88 (c, 1 in H2O). 

Me glycoside Methyl 3-amino-3-deoxy-p-D-ribofuranoside, SCI C6H13NO4 163.173 Cryst. (EtOH/petrol). Mp 108-110". 

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