1,4-Dioxane → HCID 86751607, compound

HRID 2293882Notes

Reaction equation

HRID 2293882 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]([O:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@@H:15]([CH2:35][O:36][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[O:14][C@H:10]1SCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:45]([C@H:48]([C@H:51]([O:67][C:68](=[O:75])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)/[CH:52]=[CH:53]/[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH2:49][OH:50])=[N+]=[N-].[O:76]1[CH2:81][CH2:80]OCC1>C(Cl)Cl.C1C=CC=CC=1>[C:81]([NH:45][C@H:48]([C@H:51]([O:67][C:68](=[O:75])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)/[CH:52]=[CH:53]/[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH2:49][O:50][C@H:10]1[O:14][C@H:15]([CH2:16][O:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[C@H:35]([O:36][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:39])[C@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:76])[CH2:80][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:48][CH3:49]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 109720334-Octadecene-1,3-diol, 2-azido-, 3-benzoate, (2S,3R,4E)-HCID 86751608HCID 86751608, compound

Product 1

HCID 86751607HCID 86751607, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 23443464Methane, dichloro-, compd. with benzene (1:1)Solvent

Procedure

Ethyl 2,3-di-O-benzyl-4,6-di-O-tert-butyloxycarbonylmethyl-1-thio-β-D-galactopyranoside (0.555 g, 0.88 mmol) and (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecenol (0.239 g, 0.55 mmol) were reacted by the general procedure as described in Example 1-D using methylene chloride/benzene (1:1) as solvents instead of dioxane and afforded the α-anomer (0.174 g, 31%) and the β-anomer (0.365 g, 66%) of the title compound as yellow oils.

Workup

  1. customafforded the α-anomer (0.174 g, 31%)

Sources & evidence

ORD record
ord-117c52f839544f918bdf403f9973d972
Source dataset
uspto-grants-1997_11
Patent number
US05686426

Reaction notes

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