4-Toluenesulfonyl chloride → HCID 86729320, compound

HRID 1474619Notes

Reaction equation

HRID 1474619 reaction equation
[CH2:1]([O:4][C:5]1[CH:31]=[CH:30][C:8]([CH2:9][C:10]2[CH:11]=[C:12]([C@@:17]3([O:28][CH3:29])[C@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]3)[CH:13]=[CH:14][C:15]=2[Cl:16])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]>C(OC(=O)C)C>[CH3:39][C:38]1[CH:40]=[CH:41][C:35]([S:32]([O:27][CH2:26][C@@H:19]2[C@@H:20]([OH:25])[C@H:21]([OH:24])[C@@H:22]([OH:23])[C@@:17]([C:12]3[CH:13]=[CH:14][C:15]([Cl:16])=[C:10]([CH2:9][C:8]4[CH:30]=[CH:31][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][CH:7]=4)[CH:11]=3)([O:28][CH3:29])[O:18]2)(=[O:34])=[O:33])=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86729319HCID 86729319, compound

Product 1

HCID 86729320HCID 86729320, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,3R,4S,5S,6R)-2-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (1.2 g, 2.66 mmol) in leutidine (18.6 mL, 159.8 mmol), was added tosyl chloride (3.0 g, 15.98 mmol) at 0° C. The reaction mixture was stirred at r.t. for 12 h. After the completion of reaction as monitored by TLC, the reaction mixture was diluted with ethylacetate (50 mL) and washed with 5% HCl (3×10 mL). The organic layers were dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 0.7:9.3 MeOH:DCM) to provide title compound (1.42 g, 89%).

Workup

  1. customAfter the completion of reaction
  2. washwashed with 5% HCl (3×10 mL)
  3. dry with materialThe organic layers were dried over anhydrous Na2SO4 and volatiles
  4. customwere evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 0.7:9.3 MeOH:DCM)

Sources & evidence

ORD record
ord-db75dc898ea8402d956e726eb069d139
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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