Acetic Anhydride → HCID 13191409, compound

HRID 1074430Notes

Reaction equation

HRID 1074430 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:17]([O:27][C@@H:28]2[O:41][C@H:40]([CH2:42][O:43]C(=O)C)[C@@H:35]([O:36]C(=O)C)[C@H:30]([O:31]C(=O)C)[C@H:29]2[N:47]2C(=O)C3=CC=CC=[C:49]3[C:48]2=[O:57])[C@@H:16]([CH2:58][O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[O:15][C@@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C>CO.C(N)CCC.O.CN(C)C=O>[C:1]([NH:4][C@@H:5]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:17]([O:27][C@@H:28]2[O:41][C@H:40]([CH2:42][OH:43])[C@@H:35]([OH:36])[C@H:30]([OH:31])[C@H:29]2[NH:47][C:48](=[O:57])[CH3:49])[C@@H:16]([CH2:58][O:59][CH2:60][C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[O:15][C@@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 7918Acetic AnhydrideHCID 13191407HCID 13191407, compound

Product 1

HCID 13191409HCID 13191409, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8007ButylamineSolvent

Procedure

A solution of benzyl 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (2.1 g, 2.3 mmol) in methanol (80 ml) and n-butylamine (20 ml) is heated for 48 hours at reflux temperature. Cooling and evaporation of the reaction mixture gives a solid that is slurried in water and lyophilized. The resulting solid is dissolved in the minimal volume of N,N-dimethylformamide and the solution applied to a column of silica gel (E. Merck, No. 7734, 70-230 mesh). Elution with 20:1 chloroform-methanol and evaporation of the appropriate fractions gives a chromatographically homogeneous solid that is dissolved in methanol (35 ml) and treated with acetic anhydride (2.5 ml) for 2 hours at room temperature. Evaporation of the reaction mixture and several coevaporations with toluene gives a solid that is crystallized from ethanol to afford pure benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside; yield 1.1 g (69%), m.p. 252°-256° (dec.), [α]D25 +72° (c, 1.2, methanol). The 300-MHz nmr spectrum in methanol-d4 is in accord with the desired structure.

Workup

  1. temperatureat reflux temperature
  2. temperatureCooling
  3. customevaporation of the reaction mixture
  4. customgives a solid
  5. washElution
  6. customwith 20:1 chloroform-methanol and evaporation of the appropriate fractions
  7. customgives a chromatographically homogeneous solid
  8. customEvaporation of the reaction mixture and several coevaporations with toluene
  9. customgives a solid
  10. customthat is crystallized from ethanol

Sources & evidence

ORD record
ord-5d672f68c7744858a5f104b7b247ac87
Source dataset
uspto-grants-1983_07
Patent number
US04391800

Reaction notes

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