(E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

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Chemical Name:(E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid
CAS No.:394738-17-1
Molecular Formula:C₂₁H₂₆O₉
Molecular Weight:422.432
Hs Code.:

Synonyms:(E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

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Chemical Property of (E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

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Technology Process of (E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

There total 10 articles about (E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid 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: 91.0%

: 7381-30-8
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

: 394738-16-0
(E)-3-{4-[(3aR,4S,6S,6aR)-6-acetyl-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

: 394738-17-1
(E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃;
DOI:10.1002/1521-3773(20011001)40

Reference yield:

: 394738-12-6
benzoic (2S,5S)-5-(1-benzenesulfonyl-1-nitroethyl)-2,5-dihydrofuran-2-yl ester

: 394738-17-1
(E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / (S,S)-1,2-bis(o-Ph₂P-C₆H₄-CO-NH)-cyclohexane; Et₃N / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 50 °C

2: 98 percent / OsO₄; NMO / CH₂Cl₂ / 20 °C

3: 99 percent / CH₂Cl₂ / 45 °C

4: 100 percent / p-TsOH / methanol; tetrahydrofuran / 50 °C

5: 95 percent / p-TsOH / CH₂Cl₂ / 20 °C

6: 100 percent / LiOH / methanol; H₂O; tetrahydrofuran / 50 °C

7: 80 percent / TiCl₃ / H₂O

8: 91 percent / TMSOTf / CH₂Cl₂ / 0 °C

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); lithium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; titanium(III) chloride; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; methanol; dichloromethane; water; 3: wittig reaction;
DOI:10.1002/1521-3773(20011001)40

Reference yield:

: 394738-13-7
4-[(2S,5S)-5-(1-benzenesulfonyl-1-nitroethyl)-2,5-dihydrofuran-2-yloxy]-3-(4-methoxybenzyloxy)-benzaldehyde

: 394738-17-1
(E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / N-methylmorpholine-N-oxide; aq. OsO₄ / CH₂Cl₂ / 20 °C

2: 100 percent / CH₂Cl₂ / 50 °C

3: 100 percent / p-TsOH / tetrahydrofuran; methanol / 8 h / 50 °C

4: 95 percent / p-TsOH / CH₂Cl₂ / 0.08 h / 20 °C

5: 100 percent / aq. LiOH / methanol; tetrahydrofuran / 4 h / 40 °C

6: 80 percent / aq. TiCl₃; ammonium acetate / tetrahydrofuran / 3 h / 20 °C

7: 91 percent / TMSOTf / CH₂Cl₂ / 6 h / 0 °C

With ammonium acetate; lithium hydroxide; osmium(VIII) oxide; titanium(III) chloride; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; 2: Wittig reaction;
DOI:10.1002/1521-3765(20020104)8:1<293::AID-CHEM293>3.0.CO;2-L