Cui, Jingrong published the artcileStereocontrolled allylation of 2-amino-2-deoxy sugar derivatives by a free-radical procedure, Safety of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, the publication is Carbohydrate Research (1998), 309(4), 319-330, database is CAplus.
Preparative routes for anomerically specific 1-C-allylation of 2-amino-2-deoxy sugars have been evaluated in a comparative study of various N-substituents and aglycons as precursors for glycosyl radicals that effectively capture an allyl group from allyltributyltin. The crystalline triacetate of 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-1-propene was obtained in 70% yield when 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was treated with allyltributyltin under free-radical conditions, whereas the corresponding bromide led only to an oxazolidine derivative The 2-trifluoroacetamido 1-bromide analog of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was also an effective radical source, giving the 2-trifluoroacetamido analog in 60% yield. The free amino analog was conveniently obtained via the 2-p-methoxybenzylideneamino 1-bromide analog of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride. Use of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide as radical precursor allowed stereospecific access to β-1-C-allyl derivatives of the amino sugar. The crystalline galactosamine analog was obtained by using the galacto analog of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride, but the corresponding manno chloride gave only an oxazoline product. The 1-C-allylated amino sugar derivatives are conformationally more mobile than derivatives not having a 1-C-linked substituent.
Carbohydrate Research published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Safety of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate.
Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics