D-1,4-Dithiothreitol → HCID 13696253, compound

HRID 50019Notes

Reaction equation

HRID 50019 reaction equation
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6](=[O:7])[CH:5]=[C:4](/C(/C)=C/C2C=CSC=2)[O:3]1.C(S)[C@@H](O)[C@H](O)CS>>[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6](=[O:7])[CH:5]=[CH:4][O:3]1

Participants

3

Reactant 2

HCID 446094D-1,4-DithiothreitolHCID 70035440HCID 70035440, compound

Product 1

HCID 13696253HCID 13696253, compound

Procedure

According to the procedure of Method A, Example 1, 2-methyl-5-[(E)-1-methyl-2-thien-3-ylethenyl]-2-phenylfuran-3(2H)-one was reacted with 1,4-dithio-DL-threitol to provide 5-(2-{[(2S*3S*)-2,3-dihydroxy-4-mercaptobutyl]thio}-1-methyl-2-thien-3-ylethyl)-2-methyl-2-phenylfuran-3(2H)-one as a mixture of diastereomers: 1H NMR (CDCl3) δ1.45 (m, 1H), 1.50-1.65 and 1.75-1.80 (overlapped singlets and multiplets, ˜8H), 2.40-2.70 (m, ˜4H), 3.22 (m, 1H), 3.33-3.65 (m, 2H), 4.33 (m, 1H), 5.25-5.52 (overlapped singlets, 1H), 7.05-7.60 (m, 8H); MS (HR-FAB) m/z 451.1116 (M+H calcd. for C22H27O4S3 451.1072).

Sources & evidence

ORD record
ord-4c1905b9fc6947f1b0f1a798a1850dda
Source dataset
uspto-grants-2004_03
Patent number
US06710078B2

Reaction notes

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