(E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester
CAS No.:260433-48-5
Molecular Formula:C₂₅H₃₈O₇
Molecular Weight:450.573
Hs Code.:

Synonyms:(E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester

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Chemical Property of (E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester

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Technology Process of (E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester

There total 19 articles about (E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-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:

: (E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-acrylic acid ethyl ester

: 260433-48-5
(E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;
DOI:10.1039/a908342a

Reference yield:

: 136881-05-5
(E)-3-[(2S,3S)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-oxiranyl]-acrylic acid ethyl ester

: 260433-48-5
(E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 20 steps

1.1: 92 percent / H₂O / CH₂Cl₂ / -30 °C

2.1: imidazole; DMAP / CH₂Cl₂

3.1: DIBAL-H / tetrahydrofuran / 0 °C

4.1: MCPBA / CH₂Cl₂ / 0 °C

5.1: (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

6.1: NaH / tetrahydrofuran / 0 °C

6.2: tetrahydrofuran / 0 °C

7.1: Bu₄NF / tetrahydrofuran

8.1: 97 percent / H₂O / CH₂Cl₂ / -30 °C

9.1: imidazole; DMAP / CH₂Cl₂

10.1: DIBAL-H / tetrahydrofuran / 0 °C

11.1: MCPBA / CH₂Cl₂ / 0 °C

12.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

13.1: Na[PhSeB(OEt)3]; CH₃CO₂H / ethanol / 0 °C

14.1: NaH / tetrahydrofuran / 0 °C

14.2: tetrahydrofuran / 0 °C

15.1: 99 percent / imidazole; DMAP / CH₂Cl₂

16.1: DIBAL-H / tetrahydrofuran / 0 °C

17.1: Ti(OPr-i)4; L-(+)-DET; TBHP / CH₂Cl₂ / -23 °C

18.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

19.1: NaH / tetrahydrofuran / 0 °C

19.2: tetrahydrofuran / 0 °C

20.1: Bu₄NF / tetrahydrofuran / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2R,3R)-tartrate; (COCl₂)2; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; sodium phenylseleno(triethyl)borate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Methylation / 2.1: Etherification / 3.1: Reduction / 4.1: Epoxidation / 5.1: Oxidation / 6.1: Metallation / 6.2: Condensation / 7.1: Substitution / 8.1: Methylation / 9.1: Etherification / 10.1: Reduction / 11.1: Epoxidation / 12.1: Oxidation / 13.1: Reduction / 14.1: Metallation / 14.2: Condensation / 15.1: Etherification / 16.1: Reduction / 17.1: Epoxidation / 18.1: Oxidation / 19.1: Metallation / 19.2: Condensation / 20.1: Substitution;
DOI:10.1039/a908342a

Reference yield:

: 136881-06-6
(E)-(4R,5R,6S)-7-Benzyloxy-5-hydroxy-4,6-dimethyl-hept-2-enoic acid ethyl ester

: 260433-48-5
(E)-3-[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-2,4,6-trihydroxy-3,5,7-trimethyl-octyl)-oxiranyl]-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: imidazole; DMAP / CH₂Cl₂

2.1: DIBAL-H / tetrahydrofuran / 0 °C

3.1: MCPBA / CH₂Cl₂ / 0 °C

4.1: (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.1: NaH / tetrahydrofuran / 0 °C

5.2: tetrahydrofuran / 0 °C

6.1: Bu₄NF / tetrahydrofuran

7.1: 97 percent / H₂O / CH₂Cl₂ / -30 °C

8.1: imidazole; DMAP / CH₂Cl₂

9.1: DIBAL-H / tetrahydrofuran / 0 °C

10.1: MCPBA / CH₂Cl₂ / 0 °C

11.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

12.1: Na[PhSeB(OEt)3]; CH₃CO₂H / ethanol / 0 °C

13.1: NaH / tetrahydrofuran / 0 °C

13.2: tetrahydrofuran / 0 °C

14.1: 99 percent / imidazole; DMAP / CH₂Cl₂

15.1: DIBAL-H / tetrahydrofuran / 0 °C

16.1: Ti(OPr-i)4; L-(+)-DET; TBHP / CH₂Cl₂ / -23 °C

17.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

18.1: NaH / tetrahydrofuran / 0 °C

18.2: tetrahydrofuran / 0 °C

19.1: Bu₄NF / tetrahydrofuran / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2R,3R)-tartrate; (COCl₂)2; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; sodium phenylseleno(triethyl)borate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Etherification / 2.1: Reduction / 3.1: Epoxidation / 4.1: Oxidation / 5.1: Metallation / 5.2: Condensation / 6.1: Substitution / 7.1: Methylation / 8.1: Etherification / 9.1: Reduction / 10.1: Epoxidation / 11.1: Oxidation / 12.1: Reduction / 13.1: Metallation / 13.2: Condensation / 14.1: Etherification / 15.1: Reduction / 16.1: Epoxidation / 17.1: Oxidation / 18.1: Metallation / 18.2: Condensation / 19.1: Substitution;
DOI:10.1039/a908342a