(3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide

Base Information

Chemical Name:(3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide
CAS No.:238421-74-4
Molecular Formula:C₃₁H₄₇NO₆Si
Molecular Weight:557.803
Hs Code.:

Synonyms:(3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide

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Chemical Property of (3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide

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Technology Process of (3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide

There total 9 articles about (3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide 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: 81.0%

: 4-(tert-butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-6-(2-methyl-[1,3]dioxolan-2-yl)-hexanoic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 238421-74-4
(3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide

Guidance literature:: 4-(tert-butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-6-(2-methyl-[1,3]dioxolan-2-yl)-hexanoic acid; With diphenylphosphoranyl azide; triethylamine; In toluene;

In toluene; at 80 ℃; for 1h;

benzyl alcohol; In toluene; for 16h; Heating;

Reference yield:

: 238421-61-9
(3R,5S)-3-(4-methoxyphenyl)-3-(3-oxobutyl)-5-(2-propyl)-2,4(3H,5H)-furadione

: 238421-74-4
(3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: p-TsOH*H₂O / benzene / 0.5 h / Heating; Dean-Stark apparatus

2.1: 98 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / Heating

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

4.1: 89 percent / Pb(OAc)4 / benzene / 0.08 h / 20 °C

5.1: 94 percent / benzene / 18 h / Heating

6.1: hydrogen / 5 percent Pd/C / methanol / 2 h / 20 °C

7.1: KOH / methanol; H₂O / 2 h / 45 °C

8.1: diphenylphosphynyl azide; Et₃N / toluene

8.2: toluene / 1 h / 80 °C

8.3: 81 percent / toluene / 16 h / Heating

With lead(IV) acetate; dmap; potassium hydroxide; lithium aluminium tetrahydride; diphenylphosphoranyl azide; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene; 1.1: ketalization / 2.1: Reduction / 3.1: silylation / 4.1: Oxidation / 5.1: Wittig reaction / 6.1: Hydrogenation / 7.1: Hydrolysis / 8.1: Acylation / 8.2: Rearrangement / 8.3: Addition;

Reference yield:

: 238421-40-4
(5S)-4-hydroxy-3-(4-methoxyphenyl)-5-(2-propyl)-2(5H)-furanone

: 238421-74-4
(3S)-3-(tert-butyldimethylsilyloxymethyl)-6,6-ethylenedioxy-3-(4-methoxyphenyl)-N-(benzyloxycarbonyl)heptanamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 90 percent / Et₃N / tetrahydrofuran / 24 h / 30 °C

2.1: p-TsOH*H₂O / benzene / 0.5 h / Heating; Dean-Stark apparatus

3.1: 98 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / Heating

4.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

5.1: 89 percent / Pb(OAc)4 / benzene / 0.08 h / 20 °C

6.1: 94 percent / benzene / 18 h / Heating

7.1: hydrogen / 5 percent Pd/C / methanol / 2 h / 20 °C

8.1: KOH / methanol; H₂O / 2 h / 45 °C

9.1: diphenylphosphynyl azide; Et₃N / toluene

9.2: toluene / 1 h / 80 °C

9.3: 81 percent / toluene / 16 h / Heating

With lead(IV) acetate; dmap; potassium hydroxide; lithium aluminium tetrahydride; diphenylphosphoranyl azide; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene; 1.1: Addition / 2.1: ketalization / 3.1: Reduction / 4.1: silylation / 5.1: Oxidation / 6.1: Wittig reaction / 7.1: Hydrogenation / 8.1: Hydrolysis / 9.1: Acylation / 9.2: Rearrangement / 9.3: Addition;