methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate

Base Information

Chemical Name:methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate
CAS No.:1300117-45-6
Molecular Formula:C₃₄H₅₅NO₆SSi₂
Molecular Weight:662.051
Hs Code.:

Synonyms:methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate

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Chemical Property of methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate

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Technology Process of methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate

There total 11 articles about methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-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: 90.0%

: 1300117-44-5
methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-dihydroxy-hept-4-enoate

: 69739-34-0
t-butyldimethylsiyl triflate

: 1300117-45-6
methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -40 - 0 ℃; for 2.5h;
DOI:10.1002/chem.201003265

Reference yield:

: 1196718-45-2
(3S)-1-trimethylsilyl-5-(4-methoxybenzyloxy)-1-pentyn-3-ol

: 1300117-45-6
methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C

2.1: N-Bromosuccinimide; silver nitrate / acetone / 17 h / 20 °C / Darkness

3.1: potassium phosphate; copper(ll) sulfate pentahydrate; 1,10-Phenanthroline / toluene / 12 h / 80 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.25 h / 20 °C

6.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 3 h / 20 °C

6.2: 2.5 h / 20 °C

7.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

8.1: hydrogenchloride / 4 h / Reflux

9.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -40 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium phosphate; N-Bromosuccinimide; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; silver nitrate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 7.1: Wittig rearrangement;
DOI:10.1002/chem.201003265

Reference yield:

: 1195470-99-5
5-(4-methoxybenzyloxy)-1-trimethylsilylpent-1-yne-3-ol

: 1300117-45-6
methyl (2S,3R)-3-[benzyl(4-methylbenzenesulfonyl)amino]-2,7-di(tert-butyldimethylsilyloxy)hept-4-enoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium acetate; pyridinium chlorochromate / dichloromethane; water / 2 h / 20 °C / Molecular sieve

2.1: Noyori's catalyst / isopropyl alcohol / 2.5 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C

4.1: N-Bromosuccinimide; silver nitrate / acetone / 17 h / 20 °C / Darkness

5.1: potassium phosphate; copper(ll) sulfate pentahydrate; 1,10-Phenanthroline / toluene / 12 h / 80 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.25 h / 20 °C

8.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 3 h / 20 °C

8.2: 2.5 h / 20 °C

9.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

10.1: hydrogenchloride / 4 h / Reflux

11.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -40 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium phosphate; N-Bromosuccinimide; Noyori's catalyst; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; tetrabutyl ammonium fluoride; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; silver nitrate; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 9.1: Wittig rearrangement;
DOI:10.1002/chem.201003265