(2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran>

Base Information

Chemical Name:(2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran>
CAS No.:215779-10-5
Molecular Formula:C₃₃H₄₀O₆Si
Molecular Weight:560.763
Hs Code.:

Synonyms:(2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran>

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran>

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Technology Process of (2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran>

There total 1 articles about (2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran> which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 77-76-9
2,2-dimethoxy-propane

: 195141-49-2
(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-tetrahydro-furan-3-ol

: 215779-10-5
(2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran>

Guidance literature:: With toluene-4-sulfonic acid; In acetone; for 1h; Ambient temperature;
DOI:10.1271/bbb.62.1726

Reference yield:

: 215779-10-5
(2'S,3'S,4'S)-2,2-dimethyl-1,3-dioxolane-4-spiro-3'-<2'-<(tert-butyldiphenylsilyl)oxy>methyl-4'-(3,4-methylenedioxybenzyl)tetrahydrofuran>

: (2R,3S)-2-benzyl-2-hydroxy-3-(3,4-methylenedioxybenzyl)-γ-butyrolactone

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / n-Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

2: 100 percent / I₂, PPh₃, imidazole / toluene / 1 h / Heating

3: 100 percent / Zn / ethanol / 0.5 h / Heating

4: 1.) OsO₄, NMO, 2.) NaIO₄ / 1.) acetone, t-BuOH, H₂O, room temperature, 48 h, 2.) EtOAc, H₂O, room temperature, 30 min

5: 96 percent / Ag₂CO₃, celite / toluene / 0.5 h / Heating

6: 99 percent / 1N HCl / tetrahydrofuran / 20 h / 65 °C

7: 96 percent / I₂, PPh₃, imidazole / toluene / 0.5 h / Heating

8: 84 percent / K₂CO₃ / acetone / 16 h / Ambient temperature

9: 1.) CuCN / 1.) THF, cyclohexane, Et₂O, -75 deg C to 0 deg C, 15 min, 2.) THF, -75 deg C, 1 h

With 1H-imidazole; hydrogenchloride; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Celite; tetrabutyl ammonium fluoride; iodine; potassium carbonate; triphenylphosphine; silver carbonate; zinc; In tetrahydrofuran; ethanol; acetone; toluene;
DOI:10.1271/bbb.62.1726