Allyltrimethylsilane → (2S,3R,4S,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-5-(4-ethylbenzyl)-2-methoxyphenyl)tetrahydro-2H-pyran

HRID 1713597Notes

Reaction equation

[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16]C2C=CC=CC=2)[C@H:13]([O:23][CH2:24]C2C=CC=CC=2)[C@@H:12]([CH2:31][O:32][CH2:33]C2C=CC=CC=2)[O:11][C@:10]1([C:41]1[CH:46]=[C:45]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([CH2:54][CH3:55])=[CH:50][CH:49]=2)[C:44]([Cl:56])=[CH:43][C:42]=1[O:57][CH3:58])O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:59]([Si](C)(C)C)[CH:60]=[CH2:61]>>[CH2:59]([C@:10]1([C:41]2[CH:46]=[C:45]([CH2:47][C:48]3[CH:49]=[CH:50][C:51]([CH2:54][CH3:55])=[CH:52][CH:53]=3)[C:44]([Cl:56])=[CH:43][C:42]=2[O:57][CH3:58])[C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@@H:14]([O:15][CH2:16][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:13]([O:23][CH2:24][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:11]1)[CH:60]=[CH2:61]

Participants

Reactant 2

HCID 69808Allyltrimethylsilane

HCID 68794922HCID 68794922, compound

Product 1

HCID 68789901(2S,3R,4S,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-5-(4-ethylbenzyl)-2-methoxyphenyl)tetrahydro-2H-pyranYield 159.5%

Procedure

The title compound (230 mg, 80%) was prepared from 23 (280 mg) and allyltrimethylsilane (167 μL, 120 mg, 3.0 eq.) using the method described for preparing 24.

Workup

customdescribed for preparing 24

Sources & evidence

ORD record: ord-0636fb2842634f318caaa48d9b6ba32a
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795228B2

Reaction notes

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