Trityl chloride → HCID 13633137, compound

HRID 1703948Notes

Reaction equation

HRID 1703948 reaction equation
[C:1]([O:4][C@@H:5]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:6]1[SH:7])(=[O:3])[CH3:2].[C:25]1([C:31](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:1]([O:4][C@@H:5]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:6]1[S:7][C:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 882931-Thio-beta-D-glucose 2,3,4,6-tetraacetate

Product 1

HCID 13633137HCID 13633137, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A pyridine solution (100 ml) of 35 g (0.096 mole) of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose [Methods in Carbohydrate Chemistry, Vol. 2, 436 (1963)] and 28 g (0.10 mole) of triphenylmethyl chloride was stirred at room temperature for 12 hours. The solution was filtered and the pyridine removed at reduced pressure. The residue was dissolved in chloroform (350 ml), washed with water (5 × 100 ml) and the chloroform solution dried in magnesium sulfate. The solvent was removed at reduced pressure and the residue dissolved in methanol and cooled to give 17 g (29%) of crystalline 2,3,4,6-tetra-O-acetyl-1-S-trityl-1-thio-β-D-glucopyranose, m.p. 177°-179°; [α]D25 (1% methanol) = -37.8°.

Workup

  1. filtrationThe solution was filtered
  2. customthe pyridine removed at reduced pressure
  3. dissolutionThe residue was dissolved in chloroform (350 ml)
  4. washwashed with water (5 × 100 ml)
  5. dry with materialthe chloroform solution dried in magnesium sulfate
  6. customThe solvent was removed at reduced pressure
  7. dissolutionthe residue dissolved in methanol
  8. temperaturecooled

Sources & evidence

ORD record
ord-634413bee17542baa4e6a7c0f3a15ec9
Source dataset
uspto-grants-1978_11
Patent number
US04125710

Reaction notes

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