Diethyl Ether → 8-Pentadecanyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside

HRID 74862Notes

Reaction equation

HRID 74862 reaction equation
[C:1]([O:4]O)(=[O:3])[CH3:2].[O:6]=[CH:7][C@@H:8]([C@H:10]([C@@H:12]([C@@H:14]([CH2:16][OH:17])O)[OH:13])[OH:11])[OH:9].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25](O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].B(F)(F)F.[O:38]([CH2:41][CH3:42])CC>ClCCCl>[C:1]([O:4][C@@H:14]1[C@@H:12]([O:13][C:1](=[O:3])[CH3:2])[C@H:10]([O:11][C:7](=[O:6])[CH3:8])[C@@H:8]([CH2:7][O:6][C:41](=[O:38])[CH3:42])[O:9][CH:16]1[O:17][CH:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 74245Pentadecan-8-olHCID 86658296D-glucose peracetate

Product 1

HCID 674331428-Pentadecanyl 2,3,4,6-tetra-O-acetyl-D-glucopyranosideYield 100.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of D-glucose peracetate (250 mg, 640 μmol) in DCE (1 mL) was added 8-pentadecanol (220 mg, 960 μmol). BF3.O(Et)2 (134 μL, 1.1 mmol) was added and the mixture stirred at room temperature overnight before pouring onto short plug of silica and eluting with EtOAc. The solvent was evaporated before the crude material was purified by column chromatography (SiO2, loaded with DCM, elution with DCM (100 mL), then 20% EtOAc/Hexane to 35% EtOAc/Hexane) to give the glycoside 141 as a white solid (179 mg, 50%). 1H NMR (CDCl3, 400 MHz) δ: 5.19 (dd, 1H, J2,3=9.5, J3,4=0.0, H-3), 5.06 (dd, 1H, J4,5=9.7, H-4), 4.96 (dd, 1H, J1,2=8.0, J2,3=9.6, H-2), 4.52 (d, 1H, H-1), 4.21 (dd, 1H, J5,6b=5.2, J6a,6b=12.1, H-6b), 4.12 (dd, 1H, J5,6a=2.6, H-6a), 3.66 (ddd, 1H, J4,5=10.0, H-5), 3.53 (m, 1H, CH2CHOCH2), 2.07 (s, 3H, OCOCH3), 2.02 (s, 6H, OCOCH3), 2.00 (s, 3H, OCOCH3), 1.60-1.20 (m, ˜24H, CH2), 0.88 (t, 3H, J=7.0, CH3), 0.87 (t, 31-1, J=7.0, CH3).

Workup

  1. additionbefore pouring onto short plug of silica
  2. washeluting with EtOAc
  3. customThe solvent was evaporated before the crude material
  4. customwas purified by column chromatography (SiO2
  5. washloaded with DCM, elution with DCM (100 mL)

Sources & evidence

ORD record
ord-fbbd812579b9474eab3576fa1ed53879
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

Loading…