Diisopropyl tartrate → (2R,3R)-2-Methyl-3-propyloxiranemethanol

HRID 22072

Reaction equation

[CH3:1][C@@:2]1([CH2:8][OH:9])[C@H:4]([CH2:5][CH2:6][CH3:7])[O:3]1.CC(OC([C@H](O)[C@@H](O)C(OC(C)C)=O)=O)C>>[CH3:1][C@@:2]1([CH2:8][OH:9])[C@@H:4]([CH2:5][CH2:6][CH3:7])[O:3]1

Participants

Reactant 2

HCID 6453580Diisopropyl tartrate

HCID 10931464(2R,3S)-2-Methyl-3-propyloxiranemethanol

Product 1

HCID 14959484(2R,3R)-2-Methyl-3-propyloxiranemethanolYield 79%

Procedure

Using the same procedure as for the preparation of 13, (+)-DIPT and allylic alcohol 12 gave 15 in 79% yield. 1HNMR, 13C NMR IR and high resolution MS are identical to 13. [α]D=+13.9° (c=1.35, CH2,Cl2). -P NMR (10% C6D6 in benzene, 145.786 MHz) δ:132.4 (93.2%) and 133.5 (6.8%), 86.5% ee.

Sources & evidence

ORD record: ord-bde491f3621741dfa67e25bc60bddf0e
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05426206

Linked notes

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