N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

Base Information

Chemical Name:N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide
CAS No.:1319731-17-3
Molecular Formula:C₈₂H₁₃₀N₂O₇
Molecular Weight:1255.94
Hs Code.:

N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

Synonyms:N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

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Chemical Property of N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

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Technology Process of N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

There total 13 articles about N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide 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: 71.0%

: 506-46-7
1-hexacosanoic acid

: 1319731-15-1
(S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-N-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexyl)ethane-1,2-diamine

: 1319731-17-3
N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃; Reflux; Inert atmosphere;
DOI:10.1021/ja202610x

Reference yield:

: 1319731-18-4
(3S,4R,5S,6R)-6-(benzyloxymethyl)-3,4,5-(tribenzyloxy)cyclohex-1-ene

: 1319731-17-3
N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 0 - 25 °C / Inert atmosphere

2.1: triethylamine / 0 - 25 °C / Inert atmosphere

3.1: sodium azide / N,N-dimethyl-formamide / 90 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

5.1: acetonitrile / 16 h / Reflux; Inert atmosphere

6.1: caesium carbonate; thiophenol / acetonitrile / 24 h / 25 °C / Inert atmosphere

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 20 °C / Reflux; Inert atmosphere

With lithium aluminium tetrahydride; sodium azide; borane-THF; caesium carbonate; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja202610x

Reference yield:

: 1320336-58-0
(1R,2R,3S,4S,5R,6R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl )-7-oxabicyclo[4.1.0]heptane

: 1319731-17-3
N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexylamino)ethyl)cerotamide

Guidance literature:: Multi-step reaction with 7 steps

1: lithium triethylborohydride / tetrahydrofuran / 3 h / -15 °C / Inert atmosphere

2: triethylamine / 0 - 25 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 90 °C / Inert atmosphere

4: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

5: acetonitrile / 16 h / Reflux; Inert atmosphere

6: caesium carbonate; thiophenol / acetonitrile / 24 h / 25 °C / Inert atmosphere

7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 20 °C / Reflux; Inert atmosphere

With lithium aluminium tetrahydride; sodium azide; lithium triethylborohydride; caesium carbonate; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja202610x