Dimethyl Sulfoxide → HCID 131729443, compound

HRID 1640543Notes

Reaction equation

HRID 1640543 reaction equation
[C:1]([SiH2:5][O:6][C:7]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:8]1[O:13][C@:12]([O:15][CH3:16])([CH3:14])[C@@:11]([O:18][CH3:19])([CH3:17])[O:10][C@H:9]1[CH2:20][OH:21])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.N1C(=O)CC[C@H]1C(O)=O.CS(C)=O>C(Cl)Cl.CC(=O)OCC>[C:1]([SiH2:5][O:6][C:7]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@H:8]1[O:13][C@:12]([O:15][CH3:16])([CH3:14])[C@@:11]([O:18][CH3:19])([CH3:17])[O:10][C@H:9]1[CH:20]=[O:21])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7405L-Pyroglutamic AcidHCID 81531DiisopropylethylamineHCID 131729444HCID 131729444, compound

Product 1

HCID 131729443HCID 131729443, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

[(2S,3S,5R,6R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxan-2-yl]-methanol (prepared from dimethyl L-tartrate according to J. Chem. Soc. Perkin 1 (1999), 1635; 9.2 g, 19.4 mmol) was dissolved in DCM (100 mL) and cooled to 0° C. DIPEA (19.9 mL, 6 eq.) was added and a solution of Pyr.SO3 complex (6.17 g, 2 eq.) in DMSO (27.5 mL, 20 eq.) was added dropwise over 20 min. The mixture was stirred at 0° C. for 4 h, diluted with DCM (200 mL) and washed several times with water. The org. phase was dried over MgSO4 and concentrated. The title aldehyde was isolated after FC (Hept/EA 2:1) as a colourless oil (8.6 g, 94% yield).

Workup

  1. washwashed several times with water
  2. dry with materialphase was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7bc2eb63661f4f6580a63aa41edcaf11
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

Loading…