[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

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Chemical Name:[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol
CAS No.:260433-47-4
Molecular Formula:C₃₉H₇₆O₆Si₃
Molecular Weight:725.285
Hs Code.:

Synonyms:

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Chemical Property of [(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

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Technology Process of [(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

There total 18 articles about [(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol 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)-(5R,6S,7S,8S,9S,10S)-11-Benzyloxy-6,8,10-trimethyl-5,7,9-tris-triethylsilanyloxy-undec-2-en-1-ol

: 260433-47-4
[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dichloromethane; at -23 ℃;
DOI:10.1039/a908342a

Reference yield:

: 994-30-9
triethylsilyl chloride

: 260433-47-4
[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: imidazole; DMAP / CH₂Cl₂

2.1: DIBAL-H / tetrahydrofuran / 0 °C

3.1: MCPBA / CH₂Cl₂ / 0 °C

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

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

6.1: NaH / tetrahydrofuran / 0 °C

6.2: tetrahydrofuran / 0 °C

7.1: 99 percent / imidazole; DMAP / CH₂Cl₂

8.1: DIBAL-H / tetrahydrofuran / 0 °C

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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2R,3R)-tartrate; 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: Reduction / 6.1: Metallation / 6.2: Condensation / 7.1: Etherification / 8.1: Reduction / 9.1: Epoxidation;
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

: 260433-47-4
[(2S,3S)-3-((2R,3S,4S,5S,6S,7S)-8-Benzyloxy-3,5,7-trimethyl-2,4,6-tris-triethylsilanyloxy-octyl)-oxiranyl]-methanol

Guidance literature:: Multi-step reaction with 17 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

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;
DOI:10.1039/a908342a