Publication

Synthesis of a new C(1 -> 2)-linked iminodisaccharide starting from levoglucosenone

Pierre Vogel
2002
Journal Articles

Abstract

Methyl 2-deoxy-2-[(1S)-2.5-dideoxy-2.5-imino-L-ribitol-1-C-yl)-alpha-D-glucopyr anoside ((+)-6) was obtained from the product of Nozaki-Kishi coupling of 2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropl-idene-L-ri bose ((-)-9) and 4-0-benzyl-6-O-[(benzyloxy)methyl]-3-deoxy-2-O-[(trifluoromethyl)sulfony l]-alpha-D-erythro-hex-2-enopyranosicle ((+)-12). The alkenyl triflato (+)-12 was derived from levoglucosenone (1).

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Pierre Vogel
2002
Journal Articles

Abstract

Official source

Related concepts (8)

Aldehyde

In organic chemistry, an aldehyde (ˈældᵻhaɪd) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen.

Barbier reaction

The Barbier reaction is an organometallic reaction between an alkyl halide (chloride, bromide, iodide), a carbonyl group and a metal. The reaction can be performed using magnesium, aluminium, zinc, indium, tin, samarium, barium or their salts. The reaction product is a primary, secondary or tertiary alcohol. The reaction is similar to the Grignard reaction but the crucial difference is that the organometallic species in the Barbier reaction is generated in situ, whereas a Grignard reagent is prepared separately before addition of the carbonyl compound.

Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. For example, lithium aluminium hydride is a highly reactive but useful reagent capable of reducing esters to alcohols.