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

HRID 74862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74862
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 674331428-Pentadecanyl 2,3,4,6-tetra-O-acetyl-D-glucopyranosideAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-fbbd812579b9474eab3576fa1ed53879
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828952B2

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