HCID 67771959, compound → HCID 67772293, compound

HRID 1754590Notes

Reaction equation

HRID 1754590 reaction equation
[OH:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([O:8][C@@H:9]2[CH2:18][C:17]3[C:12](=[CH:13][C:14]([OH:20])=[CH:15][C:16]=3[OH:19])[O:11][C@@H:10]2[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[O:7])=[CH:4][CH:3]=1>C(Cl)(Cl)Cl>[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][C@@H:9]2[CH2:18][C:17]3[C:12](=[CH:13][C:14]([OH:20])=[CH:15][C:16]=3[OH:19])[O:11][C@@H:10]2[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[O:7])=[CH:28][CH:29]=1

Participants

3

Reactant 1

HCID 67771959HCID 67771959, compound

Product 1

HCID 67772293HCID 67772293, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the preparation procedure of 22*, the acetylation of 10 afforded 21* with 89% yield. mp 144-145° C.; [α]D=−30.7 (c=2.5, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 7.90 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.5 Hz, 2H), 7.10 (d, J=8.5 Hz, 2H), 7.08 (d, J=8.7 Hz, 2H), 6.74 (d, J=2.2 Hz, 2H), 6.59 (d, J=2.2 Hz, 2H), 5.64 (bs, 1H), 5.22 (s, 1H), 3.12 (A of ABq, J=17.7, 4.4 Hz, 1H), 3.02 (B of ABq, J=17.7, 1.8 Hz, 1H), 2.28 (s, 6H), 2.27 (s, 3H), 2.25 (s, 3H); 13C NMR (CDCl3, 400 MHz): δ 169.1, 168.9, 168.7, 168.4, 164.8, 155.2, 154.4, 150.5, 149.7, 134.5, 131.2, 127.4, 126.9, 121.6, 109.7, 108.7, 108.0, 67.7, 26.2, 21.0, 20.7; HRMS (ESI) calcd for C30H26O11Na (M+Na) 585.1373; found 585.1371.

Workup

  1. customthe preparation procedure of 22*

Sources & evidence

ORD record
ord-b63a31f7a2954366ba64d1bb8cf2c00c
Source dataset
uspto-grants-2015_10
Patent number
US09169230B2

Reaction notes

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