(3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal

Base Information

Chemical Name:(3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal
CAS No.:260433-44-1
Molecular Formula:C₃₁H₅₈O₅Si₂
Molecular Weight:566.97
Hs Code.:

Synonyms:

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Chemical Property of (3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal

Chemical Property:

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Technology Process of (3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal

There total 15 articles about (3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal 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:

: 260433-43-0
(2R,3S)-3-((1S,2S,3S,4S,5S)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxirane-2-carbaldehyde

: 260433-44-1
(3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal

Guidance literature:: With acetic acid; sodium phenylseleno(triethyl)borate; In ethanol; at 0 ℃;
DOI:10.1039/a908342a

Reference yield:

: 81520-04-9
(2S,3S,4S)-5-(benzyloxy)-2,3-epoxy-4-methyl-1-pentanol

: 260433-44-1
(3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal

Guidance literature:: Multi-step reaction with 15 steps

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

2.1: NaH / tetrahydrofuran / 0 °C

2.2: tetrahydrofuran / 0 °C

3.1: 92 percent / H₂O / CH₂Cl₂ / -30 °C

4.1: imidazole; DMAP / CH₂Cl₂

5.1: DIBAL-H / tetrahydrofuran / 0 °C

6.1: MCPBA / CH₂Cl₂ / 0 °C

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

8.1: NaH / tetrahydrofuran / 0 °C

8.2: tetrahydrofuran / 0 °C

9.1: Bu₄NF / tetrahydrofuran

10.1: 97 percent / H₂O / CH₂Cl₂ / -30 °C

11.1: imidazole; DMAP / CH₂Cl₂

12.1: DIBAL-H / tetrahydrofuran / 0 °C

13.1: MCPBA / CH₂Cl₂ / 0 °C

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

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

With 1H-imidazole; dmap; oxalyl dichloride; (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: Oxidation / 2.1: Metallation / 2.2: Condensation / 3.1: Methylation / 4.1: Etherification / 5.1: Reduction / 6.1: Epoxidation / 7.1: Oxidation / 8.1: Metallation / 8.2: Condensation / 9.1: Substitution / 10.1: Methylation / 11.1: Etherification / 12.1: Reduction / 13.1: Epoxidation / 14.1: Oxidation / 15.1: Reduction;
DOI:10.1039/a908342a

Reference yield:

: 994-30-9
triethylsilyl chloride

: 260433-44-1
(3R,4S,5S,6S,7S,8S)-9-Benzyloxy-3-hydroxy-4,6,8-trimethyl-5,7-bis-triethylsilanyloxy-nonanal

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole; DMAP / CH₂Cl₂

2: DIBAL-H / tetrahydrofuran / 0 °C

3: MCPBA / CH₂Cl₂ / 0 °C

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

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

With 1H-imidazole; dmap; oxalyl dichloride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; sodium phenylseleno(triethyl)borate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; 1: Etherification / 2: Reduction / 3: Epoxidation / 4: Oxidation / 5: Reduction;
DOI:10.1039/a908342a