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Triethylamine → 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol

HRID 2372147
Notes
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Reaction equation

HRID 2372147 reaction equation
[CH2:1]([O:8][C@@H:9]([C@@H:12]([C@H:21]([CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:22])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([O:11][CH2:10][C@H:9]([C@@H:12]([C@H:21]([CH2:23][O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[O:22][S:40]([CH3:39])(=[O:42])=[O:41])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:42])=[O:41]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 541141622,3,5-tri-O-benzyl-L-xylitol

Product 1

HCID 539556741,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitolYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

2,3,5-Tri-O-benzyl-L-xylitol (10.2 g, 24.17 nmmol) is dissolved in dry methylene chloride (100 ml) containing triethylamine (10.1 mL, 72.5 mmol). The mixture is cooled to -10° C. and methane sulfonylchloride (3.93 mL, 50.75 mmol) is added dropwise. The mixture is stirred 30 minutes at -10° C. and washed with water. The organic layer is dried over sodium sulfate, filtered and put to dryness under reduced pressure to afford an oil. Flash chromatography on silica gel and elution with a 4:6 mixture of ethyl acetate and cyclohexane yield 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol as an oil (13.9 g, 99%).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. customto afford an oil
  5. washFlash chromatography on silica gel and elution
  6. additionwith a 4:6 mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-797587459d4f4eaa92ebf509c53f122b
Source dataset
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05097023

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes