Triacetoxyperiodinane → HCID 86759461, compound

HRID 353765Notes

Reaction equation

HRID 353765 reaction equation
[CH3:1][N:2]([CH3:59])[C@H:3]1[CH2:56][C@@H:55]([CH3:57])[O:54][CH:5]([O:6][C@@H:7]2[C@@H:23]([CH3:24])[C:22](=[O:25])[C@@H:21]([CH3:26])[C:20](=[O:27])[O:19][C@H:18]([CH2:28][CH3:29])[C@:17]3([CH2:30][OH:31])[C@H:13]([N:14]([CH2:33][CH2:34][CH2:35][CH2:36][N:37]4[CH:41]=[C:40]([C:42]5[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=5)[N:39]=[CH:38]4)[C:15](=[O:32])[O:16]3)[C@@H:12]([CH3:48])[C:11](=[O:49])[C@H:10]([CH3:50])[CH2:9][C@:8]2([O:52][CH3:53])[CH3:51])[C@@H:4]1[OH:58].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(OCC)(=O)C>[CH3:59][N:2]([CH3:1])[C@H:3]1[CH2:56][C@@H:55]([CH3:57])[O:54][CH:5]([O:6][C@@H:7]2[C@@H:23]([CH3:24])[C:22](=[O:25])[C@@H:21]([CH3:26])[C:20](=[O:27])[O:19][C@H:18]([CH2:28][CH3:29])[C@:17]3([CH:30]=[O:31])[C@H:13]([N:14]([CH2:33][CH2:34][CH2:35][CH2:36][N:37]4[CH:41]=[C:40]([C:42]5[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=5)[N:39]=[CH:38]4)[C:15](=[O:32])[O:16]3)[C@@H:12]([CH3:48])[C:11](=[O:49])[C@H:10]([CH3:50])[CH2:9][C@:8]2([O:52][CH3:53])[CH3:51])[C@@H:4]1[OH:58]

Participants

5

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 86759459HCID 86759459, compound

Product 1

HCID 86759461HCID 86759461, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (3aR,4R,7R,9R,10R,11R,13R,15R,15aR)-4-ethyl-3a-(hydroxymethyl)-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxo-1-[4-(4-pyridin-3-yl-1H-imidazol-1-yl)butyl]tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside (1 eq) in dichloromethane was added Dess-Martin Periodinane (1.1 eq). After stirring for 3 hours, more Dess-Martin Periodinane (1 eq) was added. After stirring for an additional 15 hours, the solution was diluted with ethyl acetate and was washed with 1:1 10% Na2S2O3/NaHCO3(sat), with NaCl(sat.), dried over MgSO4, filtered and concentrated. Purification by RP HPLC yielded (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-ethyl-3a-formyl-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxo-1-[4-(4-pyridin-3-yl-1H-imidazol-1-yl)butyl]tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside (19% yield) as a white solid. MH+(826.5).

Workup

  1. stirringAfter stirring for an additional 15 hours
  2. washwas washed with 1:1 10% Na2S2O3/NaHCO3(sat), with NaCl(sat.)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by RP HPLC

Sources & evidence

ORD record
ord-974718a4fdfb49e8b793fbdef538e019
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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