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Water → 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

HRID 1388312
Notes
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Reaction equation

HRID 1388312 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C@H:24]2[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]2[O:26][C:27](=[O:29])[CH3:28])[C@@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:15][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[C:52]1([S:66](Cl)(=[O:68])=[O:67])[CH:57]=[C:56]([S:58](Cl)(=[O:60])=[O:59])[CH:55]=[C:54]([S:62](Cl)(=[O:64])=[O:63])[CH:53]=1.[OH2:70]>N1C=CC=CC=1.C(#N)C.C(#N)C>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C@H:24]2[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]2[O:26][C:27](=[O:29])[CH3:28])[C@@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:15][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:66]([C:52]2[CH:57]=[C:56]([S:58]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([O:70][C@@H:6]4[O:15][C@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[C@@H:17]([O:23][C@H:24]5[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]5[O:26][C:27](=[O:29])[CH3:28])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:5]4[O:4][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=3)(=[O:60])=[O:59])[CH:55]=[C:54]([S:62]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([O:7][C@@H:6]4[O:15][C@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[C@@H:17]([O:23][C@H:24]5[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]5[O:26][C:27](=[O:29])[CH3:28])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:5]4[O:4][C:1](=[O:3])[CH3:2])=[CH:9][CH:10]=3)(=[O:64])=[O:63])[CH:53]=2)(=[O:68])=[O:67])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 889401,3,5-Benzenetrisulfonyl trichlorideHCID 132065724-Aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranoside

Product 1

HCID 16162338
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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21959178Acetonitrile pyridineSolvent

Procedure

To a solution of 2.45 g of 4-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside in pyridine:acetonitrile (1:1) was added 440 mg of 1,3,5-benzenetrisulfonyl chloride in 2 ml of acetonitrile. The mixture was stirred overnight, then poured into 250 ml of water and filtered through diatomaceous earth. The filtrate was extracted with two 100 ml portions of ethyl acetate. The extracts were combined, washed with 100 ml of 1% hydrochloric acid, then 100 ml of brine, dried and filtered through hydrous magnesium silicate. This filtrate was evaporated to a solid residue which was purified by column chromatography on silica gel using a gradient system of hexane:ethyl acetate (1:1) to (1:3). Cuts of 250 ml were taken. Fractions 11-16 were combined, evaporated and crystallized from 50 ml of ethanol, giving 1.13 g of the desired intermediate as a white powder, mp 148°-151° C.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. extractionThe filtrate was extracted with two 100 ml portions of ethyl acetate
  3. washwashed with 100 ml of 1% hydrochloric acid
  4. dry with material100 ml of brine, dried
  5. filtrationfiltered through hydrous magnesium silicate
  6. customThis filtrate was evaporated to a solid residue which
  7. customwas purified by column chromatography on silica gel using a gradient system of hexane:ethyl acetate (1:1) to (1:3)
  8. customevaporated
  9. customcrystallized from 50 ml of ethanol

Sources & evidence

ORD record
ord-8ae98af3532143f6b33a13a98f90a7a6
Source dataset
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04431637

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes