6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin

Base Information

Chemical Name:6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin
CAS No.:1154758-74-3
Molecular Formula:C₅₁H₉₄N₆O₁₈Si
Molecular Weight:1107.42
Hs Code.:

Synonyms:6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin

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Chemical Property of 6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin

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Technology Process of 6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin

There total 14 articles about 6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin 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: 56.0%

: 1154758-63-0
tert-butyl ((2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-3-(((2S,3R)-6-(aminomethyl)-3-((tert-butoxycarbonyl)amino)-3,4-dihydro-2H-pyran-2-yl)oxy)-4-((tert-butoxycarbonyl)amino)-6-((S)-4-((tert-butoxycarbonyl)amino)-2-hydroxybutanamido)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl)(methyl)carbamate

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 1154758-74-3
6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin

Guidance literature:: tert-butyl ((2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-3-(((2S,3R)-6-(aminomethyl)-3-((tert-butoxycarbonyl)amino)-3,4-dihydro-2H-pyran-2-yl)oxy)-4-((tert-butoxycarbonyl)amino)-6-((S)-4-((tert-butoxycarbonyl)amino)-2-hydroxybutanamido)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl)(methyl)carbamate; tert-butyldimethylsiloxyacetaldehyde; In 1,2-dichloro-ethane; at 40 - 50 ℃; for 4h;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 10 - 20 ℃; for 2h;

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 1154758-74-3
6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin

Guidance literature:: Multi-step reaction with 4 steps

1: potassium carbonate / 1,4-dioxane; water

2: N-hydroxy-5-norbornene-2,3-dicarboxylic acid imide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide

3: sodium hydroxide; sodium dithionite / water; ethanol / 70 °C

4: sodium cyanoborohydride / methanol / 100 °C

With sodium dithionite; N-hydroxy-5-norbornene-2,3-dicarboxylic acid imide; sodium cyanoborohydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide;

Reference yield:

: 6’-benzyloxycarbonyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S)-hydroxybutyryl]sisomicin

: 1154758-74-3
6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin

Guidance literature:: Multi-step reaction with 2 steps

1.1: 5%-palladium/activated carbon; hydrogen / methanol / 2 h / 20 - 30 °C / 827.46 Torr

2.1: 1,2-dichloro-ethane / 4 h / 40 - 50 °C

2.2: 2 h / 10 - 20 °C

With 5%-palladium/activated carbon; hydrogen; In methanol; 1,2-dichloro-ethane;