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

HRID 46226Notes

Reaction equation

HRID 46226 reaction equation
Br[C:2]1[C:3]([Cl:21])=[CH:4][C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][O:8][Si](C(C)C)(C(C)C)C(C)C.[CH2:22]([O:29][C@@H:30]1[C@@H:36]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:35]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C@@H:34]([CH2:53][O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[O:33][CH:31]1O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[Cl:20][C:5]1[CH:4]=[C:3]([Cl:21])[C:2]([CH:31]2[C@H:30]([O:29][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@@H:36]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@H:35]([O:45][CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C@@H:34]([CH2:53][O:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[O:33]2)=[CH:19][C:6]=1[CH2:7][OH:8]

Participants

3

Reactant 2

HCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose2×HCID 53329583(5-Bromo-2,4-dichlorobenzyloxy)triisopropylsilane2×

Product 1

HCID 53329750(2,4-Dichloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol

Procedure

With similar method described in Step 3 of Example 92, (5-bromo-2,4-dichlorobenzyloxy)triisopropylsilane (compound 82, 41.7 g, 101 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (compound 2, 45.4 g, 84.0 mmol) were converted to title compound (47.6 g, 81%, ca. 8:1 mixture of anomers (13:0) as a white solid.

Sources & evidence

ORD record
ord-219346c1a17348648b2e7be5de7a1262
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

Loading…