2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → (1-Methoxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)naphthalen-2-yl)methanol

HRID 46219Notes

Reaction equation

HRID 46219 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[C:4]([CH2:14][O:15][Si](C(C)C)(C(C)C)C(C)C)[CH:3]=1.[CH2:26]([O:33][C@@H:34]1[C@@H:40]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@H:39]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C@@H:38]([CH2:57][O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[O:37][CH:35]1O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH3:13][O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C@H:35]2[C@H:34]([O:33][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@@H:40]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@H:39]([O:49][CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C@@H:38]([CH2:57][O:58][CH2:59][C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[O:37]2)=[CH:3][C:4]=1[CH2:14][OH:15]

Participants

3

Reactant 2

HCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose2×HCID 67287764((4-Bromo-1-methoxynaphthalen-2-yl)methoxy)-triisopropylsilane2×

Product 1

HCID 67288992(1-Methoxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)naphthalen-2-yl)methanolYield 85%

Procedure

With similar method described in Step 3 of Example 92, ((4-bromo-1-methoxynaphthalen-2-yl)methoxy)-triisopropylsilane (compound 68b, 21.3 g, 50.3 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (compound 2, 22.6 g, 41.9 mmol) were converted to title compound (25.3 g, 85%) as a white solid.

Sources & evidence

ORD record
ord-786edd668bfc44639dcdb4dd7829a8f3
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

Loading…