Benzyl Alcohol → HCID 23392918, compound

HRID 991166Notes

Reaction equation

HRID 991166 reaction equation
[O:1]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:2]1[O:10][C@H:9]([CH2:11]O)[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@@H:3]1[OH:4].C(O)C1C=CC=CC=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[S:43](Cl)([C:46]1[CH:52]=[CH:51][C:49]([CH3:50])=[CH:48][CH:47]=1)(=[O:45])=[O:44]>C(Cl)Cl.CCOC(C)=O.CCOC(C)=O.CCCCCC>[S:43]([CH2:11][C@H:9]1[O:10][CH:2]([O:1][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])([C:46]1[CH:52]=[CH:51][C:49]([CH3:50])=[CH:48][CH:47]=1)(=[O:45])=[O:44]

Participants

8

Reactant 4

HCID 244Benzyl Alcohol2×HCID 73974-Toluenesulfonyl chlorideHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 23392919HCID 23392919, compound

Product 1

HCID 23392918HCID 23392918, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of benzyl mannopyranoside 18 (500 mg, 1.9 mmol; Synthesized via reflux in dry 1.0 Molar benzyl alcohol with 0.01 equivalents CSA, the reaction mixture is passed through a SiO2 column; benzyl alcohol comes out first using EtOAc:Hexane 1:5, then benzyl pyranoside is separated from the furanose byproduct with EtOAc as eluent) in dry pyridine (5 mL) at 0° C. was added tosyl chloride (381 mg, 2 mmol; Aldrich) dissolved in CH2Cl2 and the reaction was monitored by TLC (EtOAc). After 4 hours, the starting material was consumed completely. The reaction mixture was extracted with CH2Cl2 and washed with 1N HCl, sat. NaHCO3 and brine, and purified by flash chromatography using EtOAc as eluent to yield 531 mg (68%) of benzyl 6-tosyl-6-deoxy-D-mannopyranoside.

Workup

  1. customSynthesized
  2. custombenzyl pyranoside is separated from the furanose byproduct with EtOAc as eluent) in dry pyridine (5 mL) at 0° C.
  3. customthe starting material was consumed completely
  4. extractionThe reaction mixture was extracted with CH2Cl2
  5. washwashed with 1N HCl, sat. NaHCO3 and brine
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-f8f0a6bc9bfc41e2a69b174cf66c7f06
Source dataset
uspto-grants-2002_10
Patent number
US06462193B1

Reaction notes

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