Water → HCID 86642456, compound

HRID 2068489Notes

Reaction equation

HRID 2068489 reaction equation
[I:1][C@H:2]1[C@@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([CH2:18][OH:19])[O:12][C@@H:3]1[O:4][Si](CC)(CC)CC.C([Si](CC)(CC)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1I)C.O.FC(F)(F)C(O)=O>C1COCC1>[I:1][C@@H:2]([C@H:15]([C@@H:14]([C@@H:13]([CH2:18][OH:19])[OH:12])[OH:17])[OH:16])[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86642457HCID 86642457, compoundHCID 86642458HCID 86642458, compound

Product 1

HCID 86642456HCID 86642456, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mixture of 2-deoxy-2-iodo-1-O-triethylsilyl-α-D-mannopyranose (IX) and 1-O-triethylsilyl-2-iodo-2-deoxy-β-D-mannopyranose (VIII) (total of 3.55 g) was dissolved in THF (50 mL), water (20 mL) and trifluoroacetic acid (0.7 mL) and stirred at room temperature. Progress of the reaction was monitored by TLC and after substrate disappearance reaction mixture was washed with dichloromethane (5×10 mL). The remaining water solution was lyophilized and such obtained crude solid residue was purified by column chromatography (SilicaGel 60, Merck) using chloroform and chloroform:methanol 9:1, 7:3 as eluents, to give 2.3 g of 2-deoxy-2-iodo-D-mannose (X). Yield 90%.

Workup

  1. customafter substrate disappearance reaction mixture
  2. washwas washed with dichloromethane (5×10 mL)
  3. customsuch obtained crude solid residue
  4. customwas purified by column chromatography (SilicaGel 60, Merck)

Sources & evidence

ORD record
ord-3f94f1116c1e401e8a156ae92c04adbd
Source dataset
uspto-grants-2012_10
Patent number
US08299033B2

Reaction notes

Loading…