tert-Butyldiphenylchlorosilane → HCID 10718325, compound

HRID 967337Notes

Reaction equation

HRID 967337 reaction equation
[S:1]([CH3:13])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].Cl[Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C1C=CN=CC=1)C.ClCCCl.ClCCl>[Si:15]([O:12][CH2:11][C@H:9]1[O:10][C@@H:2]([S:1][CH3:13])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@H:7]1[OH:8])([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 94078tert-ButyldiphenylchlorosilaneHCID 10036019.beta.-D-Galactopyranoside, methyl 1-thio-

Product 1

HCID 10718325HCID 10718325, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 1-thio-β-D-galactopyranoside (25) 5 g, 28 mmol), chloro t-butyldiphenylsilane (5.85 g, 21 mmol) and DMAP (2.63 g, 21 mmol) in dry 1,2-dichloroethane (130 mL) was left to stir at reflux for 2.5 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane (200 mL) and washed with saturated sodium chloride solution (2×250 mL). The organic phase was dried over MgSO4 and subsequently evaporated to dryness to give methyl 6-O-(t-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside (26) (7.5 g, 81%) as a colorless oil.

Workup

  1. waitwas left
  2. temperatureat reflux for 2.5 h
  3. washwashed with saturated sodium chloride solution (2×250 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customsubsequently evaporated to dryness

Sources & evidence

ORD record
ord-ad8ef44fda744f829c021ed2da81fc07
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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