Thiourea → 2-S-(2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-beta-D-galactopyranosyl)-2-thiopseudourea

HRID 1155298Notes

Reaction equation

HRID 1155298 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][N:20]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])[O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[NH2:32][C:33]([NH2:35])=[S:34]>CC(C)=O>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][N:20]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])[O:7][C@H:6]1[S:34][C:33](=[NH:32])[NH2:35])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 541665552,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-alpha-D-galactopyranosyl bromide

Product 1

HCID 228184952-S-(2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-beta-D-galactopyranosyl)-2-thiopseudoureaYield 85.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-α-D-galactopyranosyl bromide (4.0 g.) and thiourea (0.67 g.) in dry acetone (20 ml.) is heated under reflux for 4 hours. The solution is evaporated in vacuo to a syrup which is partitioned between water and dichloromethane. The organic layer is reextracted with water three times. The combined aqueous extracts are evaporated to give 2-S-(2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-β-D-galactopyranosyl)-2-thiopseudourea (3.40 g.).

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solution is evaporated in vacuo to a syrup which
  3. customis partitioned between water and dichloromethane
  4. customThe combined aqueous extracts are evaporated

Sources & evidence

ORD record
ord-52ea1e5c3c7c416690420610502dd29f
Source dataset
uspto-grants-1981_11
Patent number
US04301152

Reaction notes

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