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Acetone → Amphoglucamine

HRID 435926
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HRID 435926 반응식
[CH3:1][C@@H:2]1[C@@H:41]([OH:42])[C@@H:40]([CH3:43])[C@H:39]([CH3:44])[O:38][C:36](=[O:37])[CH2:35][C@H:34]([OH:45])[CH2:33][C@H:32]([OH:46])[CH2:31][CH2:30][C@@H:29]([OH:47])[C@H:28]([OH:48])[CH2:27][C@H:26]([OH:49])[CH2:25][C@@:23]2([OH:50])[O:24][C@H:19]([C@H:20]([C:52]([OH:54])=[O:53])[C@@H:21]([OH:51])[CH2:22]2)[CH2:18][C@@H:17]([O:55][C@@H:56]2[O:61][C@H:60]([CH3:62])[C@@H:59]([OH:63])[C@H:58]([NH2:64])[C@@H:57]2[OH:65])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[CH:3]1.[NH:66]([CH2:68][C@@H:69]([C@H:71]([C@@H:73]([C@@H:75]([CH2:77][OH:78])[OH:76])[OH:74])[OH:72])[OH:70])[CH3:67].CC(C)=O.C(OCC)C>CS(C)=O>[CH3:1][C@@H:2]1[C@@H:41]([OH:42])[C@@H:40]([CH3:43])[C@H:39]([CH3:44])[O:38][C:36](=[O:37])[CH2:35][C@H:34]([OH:45])[CH2:33][C@H:32]([OH:46])[CH2:31][CH2:30][C@@H:29]([OH:47])[C@H:28]([OH:48])[CH2:27][C@H:26]([OH:49])[CH2:25][C@@:23]2([OH:50])[O:24][C@H:19]([C@H:20]([C:52]([OH:54])=[O:53])[C@@H:21]([OH:51])[CH2:22]2)[CH2:18][C@@H:17]([O:55][C@@H:56]2[O:61][C@H:60]([CH3:62])[C@@H:59]([OH:63])[C@H:58]([NH2:64])[C@@H:57]2[OH:65])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[CH:3]1.[CH3:67][NH:66][CH2:68][C@H:69]([OH:70])[C@@H:71]([OH:72])[C@H:73]([OH:74])[C@H:75]([OH:76])[CH2:77][OH:78]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 8567N-Methyl-D-glucamine2회HCID 5280965Amphotericin B

생성물 1

HCID 6449900Amphoglucamine수율 137%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

19.7 g of amphotericin B with a specific biological activity of 750 mcg/mg (ED/mg) and 14.7 g of meglumine with the content of 1-deoxy-1-(methylamino)-glucitol of at least 99% are dissolved in 100 ml of dimethylsulphoxide at a temperature within the range of from 50° to 60° C and stirred for 10 minutes. The resulting solution is added with a 7-fold volume of a mixture of acetone with diethyl ether (in a volumetric ratio of 1:1). The precipitate is filtered off, washed with the same mixture of acetone with diethyl ether, and dried at 20° C under a residual pressure of 100 mm Hg to give 32.7 g of amphoglucamine with a specific biological activity of 440 mcg/mg (ED/mg) which corresponds to the yield of 96% of amphoglucamine based on the activity of the starting amphotericin B.

후처리

  1. filtrationThe precipitate is filtered off
  2. washwashed with the same mixture of acetone with diethyl ether
  3. customdried at 20° C under a residual pressure of 100 mm Hg

출처 및 근거

ORD 기록
ord-d412bd9616854897b1590d92f597f00c
출처 데이터셋
uspto-grants-1977_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04007166

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