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

HRID 2080537Notes

Reaction equation

HRID 2080537 reaction equation
[C:1]1(=[O:12])[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].O1CCCC1.CN1CCOCC1.[CH3:25][Si:26](Cl)([CH3:28])[CH3:27]>O.C1(C)C=CC=CC=1>[CH3:25][Si:26]([CH3:28])([CH3:27])[O:3][C@@H:2]1[C@@H:4]([O:5][Si:26]([CH3:28])([CH3:27])[CH3:25])[C@H:6]([O:7][Si:26]([CH3:28])([CH3:27])[CH3:25])[C@@H:8]([CH2:9][O:10][Si:26]([CH3:28])([CH3:27])[CH3:25])[O:11][C:1]1=[O:12]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7027delta-GluconolactoneHCID 79724-MethylmorpholineHCID 8028Tetrahydrofuran

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

700.0 g of D-glucono-1,5-lactone and 7 L of tetrahydrofuran along with 3185.0 g of 4-methylmorpholine were added to a 60 L reaction vessel which was maintained at less than 5° C. 2590 g of trimethylsilyl chloride were added to the vessel and the contents were maintained at 35° C. for 5 hours. Thereafter, the vessel was cooled to 0° C. 10.5 L of toluene and 14 L of water were added to the vessel. The aqueous and organic phases were separated and the organic phase was washed with aqueous dihydrogen phosphate monohydrate to remove excess base and bring the pH of the solution to 7 to 8.

Workup

  1. temperaturewas maintained at less than 5° C
  2. temperatureThereafter, the vessel was cooled to 0° C
  3. customThe aqueous and organic phases were separated
  4. washthe organic phase was washed with aqueous dihydrogen phosphate monohydrate
  5. customto remove excess base

Sources & evidence

ORD record
ord-546dad02cf5349e7bc66f5e303259dfa
Source dataset
uspto-grants-2011_04
Patent number
US07932379B2

Reaction notes

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