HCID 44460505, compound → HCID 101307860, compound

HRID 261209Notes

Reaction equation

HRID 261209 reaction equation
[CH3:1][C:2]1[C@H:7]([OH:8])[CH2:6][C@:5]23[C@:28]4([CH3:35])[C:29]5([C@H:32]([O:34][C@@H:4]2[CH:3]=1)[CH2:33][C@H:27]4[O:26][C:24](=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]([CH:36]([OH:38])[CH3:37])[O:18][CH2:17][CH:16]([OH:39])[C:14]1([CH3:40])[O:15][CH:13]1[C:11](=[O:12])[O:10][CH2:9]3)[O:31][CH2:30]5>CO.C(Cl)(Cl)Cl>[CH3:1][C:2]1[C@H:7]([OH:8])[CH2:6][C:5]23[C@:28]4([CH3:35])[C@@:29]5([C@@H:32]([O:34][C@@H:4]2[CH:3]=1)[CH2:33][C@H:27]4[O:26][C:24](=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][C@H:19]([C@@H:36]([OH:38])[CH3:37])[O:18][CH2:17][C@H:16]([OH:39])[C@@:14]1([CH3:40])[O:15][C@@H:13]1[C:11](=[O:12])[O:10][CH2:9]3)[O:31][CH2:30]5

Participants

4

Reactant 1

HCID 44460505HCID 44460505, compound

Product 1

HCID 101307860HCID 101307860, compoundYield 0%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Preparative TLC of fraction CC on silica gel with 10% methanol in chloroform as eluent gave some baccharinol (B4) (Fraction DD) which was combined with Fraction BB as above, and a residue (Fraction EE) which was crystallized from methanol-chloroform-ether. Recrystallization from acetone-hexane gave isobaccharinol (B6, 0.20 g, 0.00037%): mp 249°-251° C.; [α]D24 +149° (c 0.66, MeOH); uv max (EtOH) λ (ε) 260 nm (20,400); ir (KBr) 3420, 1750, 1720, 1650, 1605 cm-1 ; NMR (CDCl3) ε 0.83 (3H, s, 14-H), 1.16 (3H, d, J=6 Hz, 14'-H), 1.65 (3H, s, 12'-H), 1.83 (3H, s, 16-H), 2.84, 3.13 (each 1H, d, J=4 Hz, 13-H), 3.38 (1H, s, 2'-H), 4.24, 4.46 (2H, ABq, J=12 Hz, 15-H), 5.52 (1H, d, J=5 Hz, 10-H), 5.8 (1H, m, 4-H), 5.81 (1H, d, J=11 Hz, 10'-H), 5.92 (1H, dd, J=15 and 3 Hz, 7'-H), 6.59 (1H, dd, J=11 and 11 Hz, 9'-H), 7.40 (1H, dd, J=15 and 11 Hz, 8'-H); mass spectrum (chemical ionization: methane reagent gas) m/e 563.2493 (M+ +H, calcd, for C29H39O11, 563.2492). Anal. Calcd for C29H38O11 :C, 61.91; H, 6.81. Found: C, 61.86; H, 6.85.

Workup

  1. customwas crystallized from methanol-chloroform-ether
  2. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-ceb38b5248ee4d21919e52de9cf46202
Source dataset
uspto-grants-1979_08
Patent number
US04164584

Reaction notes

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