Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diazomethane | HCID 9550 | — |
| Reactant | 1,1-O-(4,6-Dihydroxy-1,2-phenylenemethylene)-4-O-[6-O-(1-oxo-2,4-decadienyl)-β-D-galactopyranosyl]-α-D-glucopyranose 3-(7-hydroxy-8,14-dimethylhexadeca-2,4,8,10-tetraenoate) | HCID 6444369 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 131712292 | HCID 131712292 | — |
Reaction Steps
The antibiotic Papulacandin A is methylated as follows: A solution of 2 g of Papulacandin A in 100 ml of dioxan is allowed to stand at 0° C. for 30 minutes with a solution of diazomethane in ether. After having evaporated off the solvent the residue is chromatographed on a silica gel column (200 g) with chloroform and increasing amounts of methanol (5 to 20%) as eluents. Colorless, amorphous Papulacandin A-monomethyl ether is obtained after precipitation from acetone/ether/hexane. The IR-spectrum (in KBr) shows the following bands: 3500, 2970, 2950, 1710, 1645, 1625, 1465, 1445, 1350, 1270, 1155, 1065, 1035, 1010 cm-1. The UV-spectrum (in ethanol) shows the following maximum values: λmax. (εmax.): 237 (34000), 263 (41600). The 13C-NMR-spectrum shows the presence of an additional methyl group. Papulacandin A-dimethyl ether, in which the 13C-NMR-spectrum shows that two additional methyl groups are present, is obtained as further product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04278665 |
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| Source dataset | uspto-grants-1981_07 |
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| ORD ID | ord-1afc848e0b974e948f4fd379eb2bd52b |
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| Source note | uspto-grants-1981_07 |
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