Methyl 2,4-di-O-acetyl-3,6-dideoxychloroacetamido-alpha-D-mannopyranoside → methyl 3,6-dideoxyphosphonoacetamido-alpha-D-mannopyranoside

HRID 53891Notes

Reaction equation

HRID 53891 reaction equation
C([O:4][C@H:5]1[CH2:12][C@H:11]([O:13]C(=O)C)[C@@H:10]([CH3:17])[O:9][C@:6]1([NH:18][C:19](=[O:25])[CH2:20][P:21]([OH:24])([OH:23])=[O:22])[O:7][CH3:8])(=O)C.C(O[C@H]1C[C@H](OC(=O)C)[C@@H](C)O[C@]1(NC(=O)CCl)OC)(=O)C>>[P:21]([CH2:20][C:19]([NH:18][C@@:6]1([O:9][C@H:10]([CH3:17])[C@@H:11]([OH:13])[CH2:12][C@@H:5]1[OH:4])[O:7][CH3:8])=[O:25])([OH:23])([OH:24])=[O:22]

Participants

3

Reactant 2

HCID 54000006Methyl 2,4-di-O-acetyl-3,6-dideoxychloroacetamido-alpha-D-mannopyranosideHCID 86750709Methyl 2,4-di-O-acetyl-3,6-dideoxyphosphonoacetamido-alpha-D-mannopyranoside

Product 1

HCID 86750708methyl 3,6-dideoxyphosphonoacetamido-alpha-D-mannopyranoside

Procedure

Synthesis of (1S,2R,8R,8aR)-1,2,8.triacetoxy-octahydro-5-oxyindolizine 14, from Methyl 2,4-di-O-acetyl-3,6-dideoxyphosphonoacetamido-alpha-D-mannopyranoside, 9. Methyl 2,4-di-O-acetyl-3,6-dideoxychloroacetamido-alpha-D-mannopyranoside, 8, 5 g (0.02 mole) and 20 mL triethylphoside were heated at 110° C. for 15 h. The solvent was removed at high vacuum and the residual oil stirred with 50 mL hexane and stored in the freezer for 2 h. The hexane was decanted to afford methyl 3,6-dideoxyphosphonoacetamido-alpha-D-mannopyranoside, 15, as a thick white oil. TLC analysis (SiO2 /CH2Cl12 -MeOH) indicated that the compound was a single spot with Rf of 0.7 staining with 12 . This compound was evaporated from MeOH, and dried at high vacuum.

Workup

  1. customSynthesis of (1S,2R,8R,8aR)-1,2,8
  2. customThe solvent was removed at high vacuum
  3. customThe hexane was decanted

Sources & evidence

ORD record
ord-8d08fd6a3feb40c1bd410bc59f72e60f
Source dataset
uspto-grants-1997_04
Patent number
US05621106

Reaction notes

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