benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

Base Information

Chemical Name:benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate
CAS No.:329309-37-7
Molecular Formula:C₇₀H₁₂₁N₃O₁₃Si
Molecular Weight:1240.83
Hs Code.:

benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

Synonyms:benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

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Chemical Property of benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

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Technology Process of benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

There total 10 articles about benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate 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: 85.0%

: 329309-32-2
(5Z)-N-(tert-butoxycarbonyl)-N-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoic acid

: 329309-36-6
benzyl (5Z,5'Z)-N,N'-bis(tert-butoxycarbonyl)-N-[N'-(2-hydroxyethyl)-10-amino-10-methylundec-5-enoyloxyethyl]-10-amino-10-methylundec-5-enoate

: 329309-37-7
benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 14h;
DOI:10.1021/jo001247h

Reference yield:

: 109-67-1
1-penten

: 329309-37-7
benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: Mg; CuI / diethyl ether / -78 - 20 °C

1.2: 78 percent / CH₂Cl₂ / -78 - 20 °C

2.1: 92 percent Turnov_. / NaH / dimethylformamide / 96 h / 0 - 20 °C

3.1: 58 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / -78 - 20 °C

4.1: 75 percent / DMAP; Et₃N / tetrahydrofuran / 72 h / 20 °C

5.1: O₃ / various solvent(s) / 0.25 h / -78 °C

5.2: 94 percent / KN(TMS)2 / tetrahydrofuran / 2 h / -78 - 20 °C

6.1: 96 percent / DMAP; EDCI*HCl / CH₂Cl₂ / 14 h / 0 - 20 °C

7.1: 90 mg / camphor-10-sulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

8.1: 90 percent / DMAP; EDCI*HCl / CH₂Cl₂ / 14 h / 0 - 20 °C

9.1: 76 percent / camphor-10-sulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

10.1: 85 percent / DMAP; EDCI*HCl / CH₂Cl₂ / 14 h / 0 - 20 °C

With dmap; copper(l) iodide; camphor-10-sulfonic acid; sodium naphthalenide; sodium hydride; ozone; magnesium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5.2: Wittig olefination;
DOI:10.1021/jo001247h

Reference yield:

: 329309-28-6
N-(2-methylhept-6-en-2-yl)toluene-4-sulfonamide

: 329309-37-7
benzyl (5Z,5'Z,5''Z)-N,N',N''-tris(tert-butoxycarbonyl)-N-(N'-{N''-[2-(tert-butyldimethylsilyloxy)ethyl]-10-amino-10-methylundec-5-enoyloxyethyl}-10-amino-10-methylundec-5-enoyloxyethyl)-10-amino-10-methylundec-5-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent Turnov_. / NaH / dimethylformamide / 96 h / 0 - 20 °C

2.1: 58 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / -78 - 20 °C

3.1: 75 percent / DMAP; Et₃N / tetrahydrofuran / 72 h / 20 °C

4.1: O₃ / various solvent(s) / 0.25 h / -78 °C

4.2: 94 percent / KN(TMS)2 / tetrahydrofuran / 2 h / -78 - 20 °C

5.1: 96 percent / DMAP; EDCI*HCl / CH₂Cl₂ / 14 h / 0 - 20 °C

6.1: 90 mg / camphor-10-sulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

7.1: 90 percent / DMAP; EDCI*HCl / CH₂Cl₂ / 14 h / 0 - 20 °C

8.1: 76 percent / camphor-10-sulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

9.1: 85 percent / DMAP; EDCI*HCl / CH₂Cl₂ / 14 h / 0 - 20 °C

With dmap; camphor-10-sulfonic acid; sodium naphthalenide; sodium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 4.2: Wittig olefination;
DOI:10.1021/jo001247h