(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester
CAS No.:860267-63-6
Molecular Formula:C₂₈H₃₆O₅S₂
Molecular Weight:516.723
Hs Code.:

Synonyms:(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

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Chemical Property of (E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

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Technology Process of (E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

There total 6 articles about (E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester 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: 97.0%

: 860267-62-5
(2R,3R)-1,2-bis-benzyloxy-5-[1,3]dithian-2-yl-pentan-3-ol

: 623-47-2
propynoic acid ethyl ester

: 860267-63-6
(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 14h;
DOI:10.1021/ol0508126

Reference yield:

: 860267-59-0
(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

: 860267-63-6
(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

2: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

3: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

4: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

5: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

With 4-methyl-morpholine; sodium periodate; (1S)-10-camphorsulfonic acid; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Lemieux-Johnson oxidation / 5: oxy-Michael addition;
DOI:10.1021/ol0508126

Reference yield:

: 133842-56-5
Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 860267-63-6
(E)-3-[(1R,2R)-2,3-Bis-benzyloxy-1-(2-[1,3]dithian-2-yl-ethyl)-propoxy]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: CuBr / diethyl ether / 0.25 h / 0 °C

1.2: 11.2 g / diethyl ether / 2.5 h / 0 °C

2.1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

3.1: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

4.1: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

5.1: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

6.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

With 4-methyl-morpholine; sodium periodate; (1S)-10-camphorsulfonic acid; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; copper(I) bromide; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Lemieux-Johnson oxidation / 6.1: oxy-Michael addition;
DOI:10.1021/ol0508126