[(4R,5R)-2-ethoxy-5-(hydroxymethyl)-1,3-dioxolan-4-yl]methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared using the same procedure as described in Ex-1A starting from probucol and 2-ethoxy-1,3-dioxolane-4(R),5(R)-dimethanol as a white solid (10.3 g, 35%), mp 60–62° C. 1H-NMR (300 MHz, CDCl3) δ 7.56 (s, 2H), 7.44 (s, 2H), 5.89 (s, 1H), 5.36 (s, 1H), 4.75–4.78 (m, 1H), 4.19–4.24 (m, 2H), 3.92–3.99 (m, 2H), 3.84 (dd, 1H, J=10.0, 4.2 Hz), 3.60–3.74 (m, 2H), 2.79 (dd, 1H, J=9.1, 3.3 Hz). 1.43–1.45 (m, 42H), 1.28 (t, 3H, J=7.2 Hz). HRMS (ESI) calcd for C38H60O6S2 (M+Na), 699.3729; found, 699.3756. Anal. calcd. for C38H60O6S2: C, 67.42, H, 8.93, S, 9.47; found: C, 67.04, H, 9.00, S, 8.86.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared using the same procedure as described in Ex-1 starting from probucol and 2-ethoxy-1,3-dioxolane-4(R),5(R)-dimethanol. White solid, mp 69–71° C. 1H-NMR (CDCl3) δ 7.56 (s, 2H, Ph-H), 7.45 (s, 2H, Ph-H), 5.38 (s, 1H, PhOH), 4.2{tilde over (5)}4.32 (m, 1H, PhOCH2CH), 3.96 (dd, J=9, 10, 1H, CH—O—), 3.7{tilde over (2)}3.86 (m, 4H, , CH—O—), 3.0{tilde over (0)}3.40 (m, 3H, OH), 1.46 (s, 6H, S,S′-isopropylidene), 1.45 (s, 18H, tert-butyls), 1.43 (s, 18H, tert-butyls). MS m/z: 643 ([M+Na]+, 100%). Anal. calcd. for C35H56O5S2.⅓H2O: C67.05, H9.11, S, 10.23; found: C67.03, H9.06, S10.01.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared using the same procedure as described in Ex-1 starting from probucol and 2-ethoxy-1,3-dioxolane-4(R),5(R)-dimethanol. White solid, mp 69–71° C. 1H-NMR (CDCl3) δ 7.56 (s, 2H, Ph-H), 7.45 (s, 2H, Ph-H), 5.38 (s, 1H, PhOH), 4.2{tilde over (5)}4.32 (m, 1H, PhOCH2CH), 3.96 (dd, J=9, 10, 1H, CH—O—), 3.7{tilde over (2)}3.86 (m, 4H, , CH—O—), 3.0{tilde over (0)}3.40 (m, 3H, OH), 1.46 (s, 6H, S,S′-isopropylidene), 1.45 (s, 18H, tert-butyls), 1.43 (s, 18H, tert-butyls). MS m/z: 643 ([M+Na]+, 100%). Anal. calcd. for C35H56O5S2.⅓H2O: C67.05, H9.11, S, 10.23; found: C67.03, H9.06, S10.01.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared using the same procedure as described in Ex-1A starting from probucol and 2-ethoxy-1,3-dioxolane-4(R),5(R)-dimethanol as a white solid (10.3 g, 35%), mp 60–62° C. 1H-NMR (300 MHz, CDCl3) δ 7.56 (s, 2H), 7.44 (s, 2H), 5.89 (s, 1H), 5.36 (s, 1H), 4.75–4.78 (m, 1H), 4.19–4.24 (m, 2H), 3.92–3.99 (m, 2H), 3.84 (dd, 1H, J=10.0, 4.2 Hz), 3.60–3.74 (m, 2H), 2.79 (dd, 1H, J=9.1, 3.3 Hz). 1.43–1.45 (m, 42H), 1.28 (t, 3H, J=7.2 Hz). HRMS (ESI) calcd for C38H60O6S2 (M+Na), 699.3729; found, 699.3756. Anal. calcd. for C38H60O6S2: C, 67.42, H, 8.93, S, 9.47; found: C, 67.04, H, 9.00, S, 8.86.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared using the same procedure as described in Ex-1 starting from probucol and 2-ethoxy-1,3-dioxolane-4(R),5(R)-dimethanol. White solid, mp 69–71° C. 1H-NMR (CDCl3) δ 7.56 (s, 2H, Ph-H), 7.45 (s, 2H, Ph-H), 5.38 (s, 1H, PhOH), 4.2{tilde over (5)}4.32 (m, 1H, PhOCH2CH), 3.96 (dd, J=9, 10, 1H, CH—O—), 3.7{tilde over (2)}3.86 (m, 4H, , CH—O—), 3.0{tilde over (0)}3.40 (m, 3H, OH), 1.46 (s, 6H, S,S′-isopropylidene), 1.45 (s, 18H, tert-butyls), 1.43 (s, 18H, tert-butyls). MS m/z: 643 ([M+Na]+, 100%). Anal. calcd. for C35H56O5S2.⅓H2O: C67.05, H9.11, S, 10.23; found: C67.03, H9.06, S10.01.