(5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

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Chemical Name:(5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one
CAS No.:616890-50-7
Molecular Formula:C₂₃H₃₉NO₅Si
Molecular Weight:437.652
Hs Code.:

Synonyms:(5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

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Chemical Property of (5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

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Technology Process of (5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

There total 9 articles about (5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one 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: 50.0%

: 824-94-2
p-methoxybenzyl chloride

: 616890-49-4
(5S,6R)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

: 616890-50-7
(5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 5.5h;
DOI:10.1021/jm0302086

Reference yield:

: (2R)-4-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)butanal

: 616890-50-7
(5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 4.87 g / tetrahydrofuran / -78 - 20 °C

2.1: 83 percent / ethyldiisopropylamine; KI / 1,2-dimethoxy-ethane / 3 h / Heating

3.1: 81 percent / trimethylamine oxide dihydrate; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

4.1: aq. NaIO₄ / diethyl ether / 3 h / 0 °C

5.1: NaH / toluene

5.2: 1.96 g / toluene / 2 h / 0 °C

6.1: H₂ / Pd(OH)2/C / ethanol / 5 h / 20 °C / 760 Torr

7.1: 448 mg / EDCI*HCl / tetrahydrofuran / 4 h

8.1: 50 percent / NaH / dimethylformamide / 5.5 h / 20 °C

With sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium iodide; palladium dihydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5.2: Horner-Emmons reaction;
DOI:10.1021/jm0302086

Reference yield:

: 616890-44-9
(2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(dibenzylamino)butan-1-ol

: 616890-50-7
(5S,6R)-1-(4-methoxybenzyl)-6-[2-(tert-butyldimethylsilyloxy)ethyl]-5-(methoxymethoxy)piperidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 4.87 g / tetrahydrofuran / -78 - 20 °C

3.1: 83 percent / ethyldiisopropylamine; KI / 1,2-dimethoxy-ethane / 3 h / Heating

4.1: 81 percent / trimethylamine oxide dihydrate; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 5 h / 20 °C

5.1: aq. NaIO₄ / diethyl ether / 3 h / 0 °C

6.1: NaH / toluene

6.2: 1.96 g / toluene / 2 h / 0 °C

7.1: H₂ / Pd(OH)2/C / ethanol / 5 h / 20 °C / 760 Torr

8.1: 448 mg / EDCI*HCl / tetrahydrofuran / 4 h

9.1: 50 percent / NaH / dimethylformamide / 5.5 h / 20 °C

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; trimethylamine-N-oxide; hydrogen; sodium hydride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium iodide; palladium dihydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 6.2: Horner-Emmons reaction;
DOI:10.1021/jm0302086