Ammonia → N,N',N"-Tris[4-[[4-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide

HRID 1903053Notes

Reaction equation

HRID 1903053 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]([C:54]2[CH:59]=[C:58]([C:60]([NH:62][C:63]3[CH:68]=[CH:67][C:66]([S:69][C@@H:70]4[O:107][C@H:106]([CH2:108][O:109]C(=O)C)[C@@H:81]([O:82][C@H:83]5[O:100][C@H:99]([CH2:101][O:102]C(=O)C)[C@@H:94]([O:95]C(=O)C)[C@H:89]([O:90]C(=O)C)[C@H:84]5[O:85]C(=O)C)[C@H:76]([O:77]C(=O)C)[C@H:71]4[O:72]C(=O)C)=[CH:65][CH:64]=3)=[O:61])[CH:57]=[C:56]([C:113]([NH:115][C:116]3[CH:121]=[CH:120][C:119]([S:122][C@@H:123]4[O:160][C@H:159]([CH2:161][O:162]C(=O)C)[C@@H:134]([O:135][C@H:136]5[O:153][C@H:152]([CH2:154][O:155]C(=O)C)[C@@H:147]([O:148]C(=O)C)[C@H:142]([O:143]C(=O)C)[C@H:137]5[O:138]C(=O)C)[C@H:129]([O:130]C(=O)C)[C@H:124]4[O:125]C(=O)C)=[CH:118][CH:117]=3)=[O:114])[CH:55]=2)=[O:53])=[CH:47][CH:46]=1)(=O)C.N>CO>[C@H:16]1([O:15][C@@H:9]2[C@@H:8]([CH2:39][OH:40])[O:7][C@@H:6]([S:44][C:45]3[CH:50]=[CH:49][C:48]([NH:51][C:52]([C:54]4[CH:59]=[C:58]([C:60]([NH:62][C:63]5[CH:68]=[CH:67][C:66]([S:69][C@@H:70]6[O:107][C@H:106]([CH2:108][OH:109])[C@@H:81]([O:82][C@H:83]7[O:100][C@H:99]([CH2:101][OH:102])[C@@H:94]([OH:95])[C@H:89]([OH:90])[C@H:84]7[OH:85])[C@H:76]([OH:77])[C@H:71]6[OH:72])=[CH:65][CH:64]=5)=[O:61])[CH:57]=[C:56]([C:113]([NH:115][C:116]5[CH:117]=[CH:118][C:119]([S:122][C@@H:123]6[O:160][C@H:159]([CH2:161][OH:162])[C@@H:134]([O:135][C@H:136]7[O:153][C@H:152]([CH2:154][OH:155])[C@@H:147]([OH:148])[C@H:142]([OH:143])[C@H:137]7[OH:138])[C@H:129]([OH:130])[C@H:124]6[OH:125])=[CH:120][CH:121]=5)=[O:114])[CH:55]=4)=[O:53])=[CH:47][CH:46]=3)[C@H:5]([OH:4])[C@H:10]2[OH:11])[O:33][C@H:32]([CH2:34][OH:35])[C@@H:27]([OH:28])[C@H:22]([OH:23])[C@H:17]1[OH:18]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53908218N,N',N"-Tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide

Product 1

HCID 54214922N,N',N"-Tris[4-[[4-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamideYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.56 g of N,N',N"-tris-[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide in 35 ml of methanol saturated with ammonia at 0° C. was allowed to stand at ambient temperature for 6 hours. The solution was clarified by filtration and taken to dryness. The residual material was triturated with absolute ethanol and filtered giving 1.4 g of the desired intermediate as a cream-colored powder.

Workup

  1. customat 0° C.
  2. filtrationThe solution was clarified by filtration
  3. customThe residual material was triturated with absolute ethanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5f18a497d701426c9e3ab9b4aca0267d
Source dataset
uspto-grants-1984_03
Patent number
US04435387

Reaction notes

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