(2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane

Base Information

Chemical Name:(2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane
CAS No.:1352742-40-5
Molecular Formula:C₅₅H₉₃NO₄Si
Molecular Weight:860.433
Hs Code.:

Synonyms:(2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane

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Chemical Property of (2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane

Chemical Property:

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Technology Process of (2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane

There total 12 articles about (2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane 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: 68.0%

: 157905-15-2
(2S,3S)-1,3-isopropylidenedioxy-2-aminooctadecane

: 156159-42-1
(2R,3E)-2-(tert-Butyldiphenylsilyloxy)-3-octadecanoic acid

: 1352742-40-5
(2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1002/adsc.201100579

Reference yield:

: 629-74-3
hexadec-1-yne

: 1352742-40-5
(2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane

Guidance literature:: Multi-step reaction with 8 steps

1.1: ethylmagnesium bromide / diethyl ether / 6 h / Inert atmosphere; Reflux

1.2: 1.5 h / -30 °C / Inert atmosphere

2.1: (-)-(S)-alpine-borane / 16 h / 20 °C / Inert atmosphere; Neat (no solvent)

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Reflux

4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

6.1: acetic acid / tetrahydrofuran; water / 24 h / 70 °C

7.1: Jones reagent / acetone / 4 h / 0 °C

8.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; lithium aluminium tetrahydride; Jones reagent; (-)-(S)-alpine-borane; ethylmagnesium bromide; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/adsc.201100579

Reference yield:

: 15639-50-6
L-threo-dihydrosphingosine

: 1352742-40-5
(2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / chloroform / 2 h / Inert atmosphere; Reflux

2: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 0 °C / Inert atmosphere

With pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; chloroform;
DOI:10.1002/adsc.201100579