Solid-phase synthesis of oligosaccharides: construction of a dodecasaccharide was written by Nicolaou, K. C.;Watanabe, Nobuhide;Li, Jim;Pastor, Joaquin;Winssinger, Nicolas. And the article was included in Angewandte Chemie, International Edition in 1998.Name: 3-(Hydroxymethyl)-4-nitrophenol This article mentions the following:
The authors wish to report new solid-phase synthetic technol. which provides solutions to previously encountered problems, i.e. the presence of both α- and β-anomers at every cleavage stage and the need to reactivate the cleavage product prior to its possible reincorporation into the growing oligosaccharide chain on the solid phase, by incorporating an appropriate spacer (p-hydroxybenzoic acid) between the photolabile linker (4-hydroxy-2-nitrobenzyl alc.) and the anomeric position of the first glycoside, and which appears ideal for block-type oligosaccharide synthesis. The new technol. has advantages such as convergence for block-type construction, high yielding glycosidation steps, maintenance of stereochem. integrity during loading and unloading, and flexibility and allowed the construction of the stereochem. homogeneous dodecasaccharide (I; TBDPS = tert-butyldiphenylsilyl, Bz = benzoyl, Bn = benzyl) related to the phytoalexin elicitor family, which represents the largest oligosaccharide to be constructed on solid phase thus far. By virtue of its generality, this method could prove highly enabling for the construction of large and diverse combinatorial libraries of oligosaccharides. Thus, 5-hydroxy-2-nitrobenzaldehyde was loaded onto Merrifield resin in the presence of Cs2CO3 and Bu4NI followed by NaBH4 reduction to afford resin (II; R = H) which was condensed with 2,3,4-tetra-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-O-(p-hydroxybenzoyl)-β-
3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Name: 3-(Hydroxymethyl)-4-nitrophenol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts