Triacetoxyperiodinane → HCID 66750620, compound

HRID 643907Notes

Reaction equation

HRID 643907 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N:20]2[S:24](=[O:26])(=[O:25])[N:23]([CH2:27][O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:22](=[O:36])[CH2:21]2)=[CH:11][C:12]2[CH2:13][CH2:14][CH:15]([OH:19])[CH2:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:29]([O:28][CH2:27][N:23]1[C:22](=[O:36])[CH2:21][N:20]([C:10]2[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:18][C:17]3[CH2:16][C:15](=[O:19])[CH2:14][CH2:13][C:12]=3[CH:11]=2)[S:24]1(=[O:25])=[O:26])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66750752HCID 66750752, compound

Product 1

HCID 66750620HCID 66750620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-(3-benzyloxy-6-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-benzyloxymethyl-1,1-dioxo-1,2,5-thiadiazolidin-3-one (87.6 mg, 0.17 mmol) in DCM (3 mL) is added to a suspension of Dess-Martin reagent (80 mg, 0.19 mmol) in DCM (1 mL). The mixture is stirred at RT for 30 min and filtered through Celite. The filtrate is concentrated and purified by chromatography to give the title compound as an oil: 1H NMR (CDCl3) δ 2.54 (t, J=7 Hz, 2H), 3.01 (t, J=7 Hz, 2H), 3.55 (s, 2H), 4.44 (s, 2H), 4.57 (s, 2H), 5.03 (s, 2H), 5.8 (s, 2H), 6.82 (s, 1H), 7.28-7.36 (m, 11H); (M+NH4)+=524.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate is concentrated
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-62e93de443b44db79191cfe7d195103d
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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