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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2307733Erstellt: 26. Oktober 2026

Methyl Glycolate → 1-o-Methyloxycarbonylmethyl-2,3,4,6-tetra-o-acetyl-glucopyranose

https://huagongshe.com/reaction/2307733

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktMethyl GlycolateHCID 66774—
Eduktalpha-D-Glucopyranosyl bromide, tetraacetateHCID 101776—
KatalysatorMercury dibromideHCID 24612—
KatalysatorMercuric oxideHCID 30856—
Produkt1-o-Methyloxycarbonylmethyl-2,3,4,6-tetra-o-acetyl-glucopyranoseHCID 2074473860%

Reaktionsschritte

The yields of the compounds of general formula I, which can be achieved with the process according to the invention, are good. For known compounds in which a comparison with the prior art is possible, they exceed the yields of the prior art. Thus, for example, (WO 96/35700), in the reaction of acetobromoglucose with glycolic acid methyl ester under the influence of mercury oxide and mercury(II) bromide according to Koenigs-Knorr, the 1-O-methyloxycarbonylmethyl-2,3,4,6-tetra-O-acetyl-glucopyranose is obtained with a yield of 60%. The saponification to the free acid would be connected with a further loss in yield. EP 882733 also describes the production of this compound, but without yield information. According to the process of the invention, the acid is also obtained in a two-stage process. Here, the yield is 78%, however (Example 24 of this application).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06831164B2
Quelldatensatzuspto-grants-2004_12
ORD IDord-80430e322fcc4d44bda2ed881baf8ab4
Quellennotizuspto-grants-2004_12