Valienamine → HCID 131719634, compound

HRID 1898796Notes

Reaction equation

HRID 1898796 reaction equation
[CH:1]1[C@H:6]([NH2:7])[C@H:5]([OH:8])[C@@H:4]([OH:9])[C@H:3]([OH:10])[C:2]=1[CH2:11][OH:12].C1[C@H](N)[C@H]([OH:20])[C@@H](O)[C@H](O)C=1CO.O=[CH:26][C@@H:27]([C@H:29]([C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32])[OH:30])[OH:28]>C(O)CC>[CH2:1]1[C@:2]([OH:20])([CH2:11][OH:12])[C@@H:3]([OH:10])[C@H:4]([OH:9])[C@@H:5]([OH:8])[C@H:6]1[NH2:7].[CH2:35]1[O:36][C@@H:26]2[O:34][C@H:33]1[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]2[OH:28]

Participants

4

Reactant 2

HCID 193758ValienamineHCID 131719635HCID 131719635, compound

Product 1

HCID 131719634HCID 131719634, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of protected valienamine, (1R)-(1,2,4/3)-2,3,4-tribenzyl-5-benzyloxy-methylcyclohex-5-enylamine, (Compound 1) made according to the method of Ogawa et al. J. Chem. Soc. Perkin Trans (1988)3 (1.41 g, 2.63 mmol). This was combined with the protected epoxide, 1,6-anhydro-4-O-benzyl-2,3-epoxy-glucose, made according to the method set forth in Cerny et al., J. Czechoslav. Chem. Commun 39 (1974)4 (compound 2) (3.28 g, 14.0 mmol), in n-propanol (28 ml) and was heated at 90° C. for 4 days. Solvent was evaporated, then co-evaporated with toluene and the residue was chromatographed on a silica gel column using hexane:ethylacetate (2:1) as eluent to provide 1,6-anhydro-4-O-benzyl-2-deoxy-2-[1D-(1N,2,4/3)-(2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-β-D-glucopyranose (compound 3) (1.2 g, 59.2%).

Workup

  1. customSolvent was evaporated
  2. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-af239bd8098f45449860b9c39d28428d
Source dataset
uspto-grants-1996_11
Patent number
US05571796

Reaction notes

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