N,N'-Bis[4-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosylthio]phenyl]octanediamide → N,N'-Bis[4-[4-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranosylthio]phenyl]octanediamide

HRID 434741Notes

Reaction equation

HRID 434741 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15][C@H:16]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C)[C@@H:27]([O:28]C(=O)C)[C@H:22]([O:23]C(=O)C)[C@H:17]2[O:18]C(=O)C)[C@@H:8]([CH2:39][O:40]C(=O)C)[O:7][C@H:6]1[S:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][C:52](=[O:112])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:59]([NH:61][C:62]2[CH:67]=[CH:66][C:65]([S:68][C@@H:69]3[O:106][C@H:105]([CH2:107][O:108]C(=O)C)[C@@H:80]([O:81][C@H:82]4[O:99][C@H:98]([CH2:100][O:101]C(=O)C)[C@@H:93]([O:94]C(=O)C)[C@H:88]([O:89]C(=O)C)[C@H:83]4[O:84]C(=O)C)[C@H:75]([O:76]C(=O)C)[C@H:70]3[O:71]C(=O)C)=[CH:64][CH:63]=2)=[O:60])=[CH:47][CH:46]=1)(=O)C>CO.N>[C@H:82]1([O:81][C@@H:80]2[C@@H:105]([CH2:107][OH:108])[O:106][C@@H:69]([S:68][C:65]3[CH:66]=[CH:67][C:62]([NH:61][C:59](=[O:60])[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][C:52]([NH:51][C:48]4[CH:47]=[CH:46][C:45]([S:44][C@@H:6]5[O:7][C@H:8]([CH2:39][OH:40])[C@@H:9]([O:15][C@H:16]6[O:33][C@H:32]([CH2:34][OH:35])[C@@H:27]([OH:28])[C@H:22]([OH:23])[C@H:17]6[OH:18])[C@H:10]([OH:11])[C@H:5]5[OH:4])=[CH:50][CH:49]=4)=[O:112])=[CH:63][CH:64]=3)[C@H:70]([OH:71])[C@H:75]2[OH:76])[O:99][C@H:98]([CH2:100][OH:101])[C@@H:93]([OH:94])[C@H:88]([OH:89])[C@H:83]1[OH:84]

Participants

4

Reactant 1

HCID 53876502N,N'-Bis[4-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosylthio]phenyl]octanediamide

Product 1

HCID 54443576N,N'-Bis[4-[4-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranosylthio]phenyl]octanediamide

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A 28.4 g portion of N,N'-bis[4-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosylthio]phenyl]octanediamide was dissolved in a 0° C. solution of 500 ml of methanol saturated with ammonia. The solution was allowed to stand at 0° C., under an inert atmosphere, for 18 hours, then was warmed to ambient temperature and evaporated. The residue was triturated with 200 ml of absolute ethanol, filtered, washed in sequence with absolute ethanol, acetonitrile, then ether and dried in vacuo at 40° C., giving 12.1 g of the desired intermediate as an amorphous solid.

Workup

  1. customevaporated
  2. customThe residue was triturated with 200 ml of absolute ethanol
  3. filtrationfiltered
  4. washwashed in sequence with absolute ethanol, acetonitrile
  5. dry with materialether and dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-c6f353979f174a99bde54c623e004ef0
Source dataset
uspto-grants-1983_08
Patent number
US04399126

Reaction notes

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