Chloroform → HCID 13633137, compound

HRID 839572Notes

Reaction equation

HRID 839572 reaction equation
Br.[C:2]([O:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][C@H:7]1[S:25]C(=N)N)(=[O:4])[CH3:3].C(Cl)(Cl)Cl.[C:33](Cl)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>N1C=CC=CC=1>[C:33]([S:25][C@@H:7]1[O:8][C@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:5][C:2](=[O:4])[CH3:3])([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6456Trityl chlorideHCID 1159829040591-65-9

Product 1

HCID 13633137HCID 13633137, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranose, obtained from the hydrolysis of 29 g. of S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thiopseudourea hydrobromide as in "Methods in Carbohydrate Chemistry", Vol. II, page 436 (Whistler and Wolfrom editors, Academic Press Inc., 1963), was dissolved in 250 ml. of chloroform and cooled to 0°-5° C. in an ice bath. Anhydrous pyridine (20 ml.) was added, followed by 27.9 g. of trityl chloride. The mixture was stirred overnight at ambient temperature and the organic solution was extracted with dilute hydrochloric acid, washed with 5% aqueous sodium carbonate solution and with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from ether, then recrystallized from benzene-cyclohexane to give S-trityl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose, m.p. 177.5°-179.5° C.

Workup

  1. extractionthe organic solution was extracted with dilute hydrochloric acid
  2. washwashed with 5% aqueous sodium carbonate solution and with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from ether
  6. customrecrystallized from benzene-cyclohexane

Sources & evidence

ORD record
ord-49ef84f638c74b069739592e5896ce77
Source dataset
uspto-grants-1978_06
Patent number
US04096249

Reaction notes

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