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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 354629Generated: October 30, 2026

Chloroform → [(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18R,19Z,21Z)-2,15,17,29-tetrahydroxy-18-(hydroxymethyl)-11-methoxy-3,7,12,14,16,22-hexamethyl-6,23,26,27-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl] acetate

https://huagongshe.com/reaction/354629

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroformHCID 6212—
ReactantEthyl AcetateHCID 8857—
Reactant[(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,26,27-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl] acetateHCID 102115525—
SolventAcetoneHCID 180—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product[(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18R,19Z,21Z)-2,15,17,29-tetrahydroxy-18-(hydroxymethyl)-11-methoxy-3,7,12,14,16,22-hexamethyl-6,23,26,27-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl] acetateHCID 102115528—

Reaction Steps

In order to manufacture small quantities of 3-hydroxyrifamycin S in pure form, it is advantageous to use preparative thin-layer chromatography; suitable eluants for this purpose are, for example, silica gel thin-layer plates (like the above-mentioned plates F 254) and a mixture of chloroform and methanol (4:1 or 6:1), or of ethyl acetate, acetone and water (72:24:4) or of toluene, acetone and methanol (5:3:2). 3,31-Dihydroxyrifamycin S and 1-desoxy-1-oxarifamycin S are obtained in pure form in an analogous manner using the same plates and elution systems. The desired zone is separated off mechanically, collected and extracted with a suitable solvent, preferably ethyl acetate, in order to isolate the pure product. If necessary, this purification process can be repeated using various adsorbents and/or solvent combinations.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04376166
Source datasetuspto-grants-1983_03
ORD IDord-02bd169ee9f2421c8f7b22b66d2df5db
Source noteuspto-grants-1983_03