(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester

Base Information

Chemical Name:(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester
CAS No.:860267-64-7
Molecular Formula:C₂₅H₃₂O₆
Molecular Weight:428.525
Hs Code.:

Synonyms:(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester

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Chemical Property of (2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester

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Technology Process of (2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester

There total 8 articles about (2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic 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: 86.0%

: 860267-58-9
(1'R,1''R)-3-[1'-(1'',2''-dibenzyloxyethyl)-4'-oxo-butoxy]-acrylic acid ethyl ester

: 860267-64-7
(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester

Guidance literature:: With methanol; samarium diiodide; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ol0508126

Reference yield:

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

: 860267-64-7
(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

7: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

With 4-methyl-morpholine; methanol; sodium periodate; samarium diiodide; (1S)-10-camphorsulfonic acid; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; methyl iodide; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; 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

: 860267-64-7
(2'R,3'S,6'R,1''R)-[6'-(1'',2''-bis-benzyloxy-ethyl)-3'-hydroxy-tetrahydropyran-2'-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 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

7.1: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

8.1: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

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