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

HRID 2223473Notes

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

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

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

Sources & evidence

ORD record: ord-249bae74665d442089be13b3ab2c1dd1
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375213B2

Reaction notes

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