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

HRID 1388313Notes

Reaction equation

HRID 1388313 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[O:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][S:52]([C:55]2[CH:60]=[C:59]([S:61]([NH:64][C:65]3[CH:70]=[CH:69][C:68]([O:71][C@@H:72]4[O:109][C@H:108]([CH2:110][O:111]C(=O)C)[C@@H:83]([O:84][C@H:85]5[O:102][C@H:101]([CH2:103][O:104]C(=O)C)[C@@H:96]([O:97]C(=O)C)[C@H:91]([O:92]C(=O)C)[C@H:86]5[O:87]C(=O)C)[C@H:78]([O:79]C(=O)C)[C@H:73]4[O:74]C(=O)C)=[CH:67][CH:66]=3)(=[O:63])=[O:62])[CH:58]=[C:57]([S:115]([NH:118][C:119]3[CH:124]=[CH:123][C:122]([O:125][C@@H:126]4[O:163][C@H:162]([CH2:164][O:165]C(=O)C)[C@@H:137]([O:138][C@H:139]5[O:156][C@H:155]([CH2:157][O:158]C(=O)C)[C@@H:150]([O:151]C(=O)C)[C@H:145]([O:146]C(=O)C)[C@H:140]5[O:141]C(=O)C)[C@H:132]([O:133]C(=O)C)[C@H:127]4[O:128]C(=O)C)=[CH:121][CH:120]=3)(=[O:117])=[O:116])[CH:56]=2)(=[O:54])=[O:53])=[CH:47][CH:46]=1)(=O)C>CO>[C@H:16]1([O:15][C@@H:9]2[C@@H:8]([CH2:39][OH:40])[O:7][C@@H:6]([O:44][C:45]3[CH:50]=[CH:49][C:48]([NH:51][S:52]([C:55]4[CH:56]=[C:57]([S:115]([NH:118][C:119]5[CH:120]=[CH:121][C:122]([O:125][C@@H:126]6[O:163][C@H:162]([CH2:164][OH:165])[C@@H:137]([O:138][C@H:139]7[O:156][C@H:155]([CH2:157][OH:158])[C@@H:150]([OH:151])[C@H:145]([OH:146])[C@H:140]7[OH:141])[C@H:132]([OH:133])[C@H:127]6[OH:128])=[CH:123][CH:124]=5)(=[O:117])=[O:116])[CH:58]=[C:59]([S:61]([NH:64][C:65]5[CH:66]=[CH:67][C:68]([O:71][C@@H:72]6[O:109][C@H:108]([CH2:110][OH:111])[C@@H:83]([O:84][C@H:85]7[O:102][C@H:101]([CH2:103][OH:104])[C@@H:96]([OH:97])[C@H:91]([OH:92])[C@H:86]7[OH:87])[C@H:78]([OH:79])[C@H:73]6[OH:74])=[CH:69][CH:70]=5)(=[O:63])=[O:62])[CH:60]=4)(=[O:53])=[O:54])=[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

3

Reactant 1

HCID 16162338N,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]oxy]phenyl]-1,3,5-benzenetrisulfonamide

Product 1

HCID 13274731N,N',N"-Tris[4-[(4-O-alpha-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]phenyl]-1,3,5-benzenetrisulfonamideYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 800 mg 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]oxy]phenyl]-1,3,5-benzenetrisulfonamide in 15 ml of methanol was cooled in an ice-water bath, then ammonia was bubbled in, with stirring for one hour. The cooling bath was removed and stirring was continued for 4 days. The solvents were evaporated and the residue was heated in vacuo at 110° C. for 2 hours. This residue was crystallized from a mixture of methanol and ethanol, giving 280 mg of the desired intermediate as a white powder, mp 206°-210° C.

Workup

  1. temperaturewas cooled in an ice-water bath
  2. customammonia was bubbled in,
  3. customThe cooling bath was removed
  4. stirringstirring
  5. waitwas continued for 4 days
  6. customThe solvents were evaporated
  7. customThis residue was crystallized from a mixture of methanol and ethanol

Sources & evidence

ORD record
ord-7c8ee2c6b3c74e828f1efc72ac4de2f7
Source dataset
uspto-grants-1984_02
Patent number
US04431637

Reaction notes

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