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

HRID 1713598Notes

Reaction equation

HRID 1713598 reaction equation
[CH2:1]([C@:4]1([C:43]2[CH:48]=[C:47]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[C:46]([Cl:58])=[CH:45][C:44]=2[O:59]C)[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:8]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:7]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:6]([CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:5]1)[CH:2]=[CH2:3]>O>[CH2:1]([C@:4]1([C:43]2[CH:48]=[C:47]([CH2:49][C:50]3[CH:51]=[CH:52][C:53]([CH2:56][CH3:57])=[CH:54][CH:55]=3)[C:46]([Cl:58])=[CH:45][C:44]=2[OH:59])[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:8]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@H:7]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:6]([CH2:34][O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[O:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 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-pyran

Product 1

HCID 687951322-((2S,3R,4S,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)-5-chloro-4-(4-ethylbenzyl)phenolYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34 (500 mg, 98% yield) was prepared from 33 (520 mg) using the same procedure used to prepare 25. 1H NMR (300 MHz, CDCl3) δ 8.95 (s, 1H), 7.20-7.39 (m, 18H), 6.87-7.14 (m, 10H), 5.48-5.62 (m, 1H), 4.75-4.99 (m, 5H), 4.65 (d, J=12 Hz, 1H), 4.38-4.49 (m, 3H), 3.69-4.02 (m, 9H), 3.52-3.58 (m, 1H), 3.03 (dd, J=6.3, 16.2 Hz, 1H), 2.75 (dd, J=6.3, 16.2 Hz, 1H), 2.55 (q, J=7.5 Hz, 2H), 1.17 (t, J=7.5 Hz, 3H). LC/MS m/z 827 (M+H+water), 832 (M+Na).

Workup

  1. customto prepare 25

Sources & evidence

ORD record
ord-d2b535c6a672473db18cd5a38d1d188d
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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