Methanol → HCID 87309028, compound

HRID 1854256Notes

Reaction equation

HRID 1854256 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([N:11]=[C:12]=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2].[CH3:27][OH:28]>>[C:1]([O:4][C@@H:5]1[C@H:10]([NH:11][C:12]([O:28][CH3:27])=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 14130735(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetate

Product 1

HCID 87309028HCID 87309028, compoundYield 92%

Procedure

A solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (1.0 g, 2.57 mmol) in anhydrous methanol (10 mL) was heated to reflux. The reaction was complete after 1 h as determined by TLC. The solvent was removed in vacuo. The product was then purified by flash column silica chromatography using a solvent system of 3:1 hexanes/EtOAc, which provided (2R,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(methoxycarbonothioylamino)-tetrahydro-2H-pyran-2,4,5-triyl triacetate (1.0 g, 92% yield) as a slightly yellow syrup. 1H NMR (500 MHz, CDCl3) δ 2.11 (s, 3H), 2.12 (s, 6H), 3.81 (ddd, 1H), 3.95 (s, 3H), 4.1 (m, 2H), 4.31 (m, 1H), 5.17 (m, 2H), 5.73 (d, 1H, J=8.6 Hz), 6.21 (d, 1H, J=10.0 Hz).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe product was then purified by flash column silica chromatography

Sources & evidence

ORD record
ord-63e90254170b4d40825c5c0323220af7
Source dataset
uspto-grants-2015_02
Patent number
US08962664B2

Reaction notes

Loading…