HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2307733Generated: October 25, 2026
Methyl Glycolate → 1-o-Methyloxycarbonylmethyl-2,3,4,6-tetra-o-acetyl-glucopyranose
https://huagongshe.com/reaction/2307733
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Glycolate | HCID 66774 | — |
| Reactant | alpha-D-Glucopyranosyl bromide, tetraacetate | HCID 101776 | — |
| Catalyst | Mercury dibromide | HCID 24612 | — |
| Catalyst | Mercuric oxide | HCID 30856 | — |
| Product | 1-o-Methyloxycarbonylmethyl-2,3,4,6-tetra-o-acetyl-glucopyranose | HCID 20744738 | 60% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06831164B2 |
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| Source dataset | uspto-grants-2004_12 |
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| ORD ID | ord-80430e322fcc4d44bda2ed881baf8ab4 |
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| Source note | uspto-grants-2004_12 |
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