(3R,4S,5R,6R)-3,4,5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-on → delta-Gluconolactone

HRID 718215Notes

Reaction equation

HRID 718215 reaction equation
C[Si](C)(C)[O:3][C@@H:4]1[C@@H:9]([O:10][Si](C)(C)C)[C@H:8]([O:15][Si](C)(C)C)[C@@H:7]([CH2:20][O:21][Si](C)(C)C)[O:6][C:5]1=[O:26]>CCCCCCC>[CH2:20]([OH:21])[C@H:7]1[O:6][C:5](=[O:26])[C@H:4]([OH:3])[C@@H:9]([OH:10])[C@@H:8]1[OH:15]

Participants

3

Reactant 1

HCID 10994280(3R,4S,5R,6R)-3,4,5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-on

Product 1

HCID 7027delta-Gluconolactone

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A 100 mL flask was charged with (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one (6.54 g) and n-heptane (10.2 mL), and stirred for 10 min under argon sparging. The mixture was cooled to −20° C. to −30° C. under nitrogen atmosphere. The solution was added to a suitable cooled addition funnel and was kept ready for addition to the aryl magnesium.

Workup

  1. temperatureThe mixture was cooled to −20° C. to −30° C. under nitrogen atmosphere
  2. additionThe solution was added to
  3. temperaturea suitable cooled
  4. additionaddition funnel

Sources & evidence

ORD record
ord-ad70a151d2654a49b969a117f327b096
Source dataset
uspto-grants-2015_11
Patent number
US09193751B2

Reaction notes

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