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

HRID 46230Notes

Reaction equation

HRID 46230 reaction equation
Br[C:2]1[C:3]([O:21][CH3:22])=[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.[CH2:23]([O:30][C@@H:31]1[C@@H:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:36]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:35]([CH2:54][O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[O:34][CH:32]1O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Cl:20][C:5]1[CH:4]=[C:3]([O:21][CH3:22])[C:2]([CH:32]2[C@H:31]([O:30][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@@H:37]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@H:36]([O:46][CH2:47][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[C@@H:35]([CH2:54][O:55][CH2:56][C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[O:34]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 53329406(5-Bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane2×

Product 1

HCID 53329585(2-Chloro-4-methoxy-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-chloro-4-methoxybenzyloxy)triisopropylsilane (compound 89, 27.2 g, 66.7 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (compound 2, 30.0 g, 55.6 mmol) were converted to title compound (22.6 g, 59%, ca. 8:1 mixture of anomers (13:0) as a white solid.

Sources & evidence

ORD record
ord-2c3a65c066ad4c4fa274a5b279ee8e5d
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

Loading…