Allyl Alcohol → HCID 67541844, compound

HRID 2408166Notes

Reaction equation

[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH2:13](O)C=C.Cl[C:18](Cl)(Cl)[C:19]([O:21][C@H:22]1[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:23]1[NH:41][C:42](=[O:47])[C:43]([Cl:46])([Cl:45])[Cl:44])=N.CCOC(C)=O>C(Cl)Cl.C(N(CC)CC)C>[C:26]([O:25][C@H:24]1[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[O:35][C@@H:22]([O:21][CH2:19][CH:18]=[CH2:13])[C@@H:23]1[NH:41][C:42](=[O:47])[C:43]([Cl:46])([Cl:45])[Cl:44])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

TMSOTf (830.0 μL, 4.6 mmol, 0.2 eq.) is added to a solution of allyl alcohol (3.1 mL, 46.0 mmol, 2 eq.) and of donor 1 (13.7 g, 23.0 mmol, 1 eq.) in DCM (160 mL), in the presence of molecular sieve 4 Å (8.9 g), stirred under argon at −78° C. After stirring for 30 min, monitoring by TLC (Tol/EtOAc, 8/2) indicates the disappearance of the donor (Rf=0.5) and the appearance of a new, more polar compound (Rf=0.35). The reaction is stopped by adding triethylamine (1 mL) and then the reaction mixture is filtered and concentrated in a rotary evaporator. The yellow oil obtained is purified by silica gel chromatography (Tol/EtOAc, 9/1→75/25) to obtain the allyl glycoside 18 as a white solid (9.4 g, 83%).

Workup

stirringAfter stirring for 30 min
filtrationthe reaction mixture is filtered
concentrationconcentrated in a rotary evaporator
customThe yellow oil obtained
customis purified by silica gel chromatography (Tol/EtOAc, 9/1→75/25)

Sources & evidence

ORD record: ord-92acde57cb324feebabbe57e3641917d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815239B2

Reaction notes

Loading…