N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide
• CAS No.: 350027-59-7
• Molecular Formula: C₂₈H₃₃NO₇S₂
• Molecular Weight: 559.705

Synonyms:N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide

Chemical Property of N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide

Chemical Property:

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Technology Process of N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide

There total 3 articles about N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide 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: 95.0%

(S)-ethyl 2-(4-methylphenylsulfonamido)-3-phenylpropanoate (28709-72-0) + 1-(3,3-dimethoxypropylsulfonyl)-4-methylbenzene (104755-40-0) → N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide (350027-59-7)

Guidance literature:

1-(3,3-dimethoxypropylsulfonyl)-4-methylbenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

(S)-ethyl 2-(4-methylphenylsulfonamido)-3-phenylpropanoate; In tetrahydrofuran; at -78 - -30 ℃; for 1.5h;

DOI:10.1016/S0022-328X(00)00918-9

Reference yield:

(L)-phenylalanine ethyl ester hydrochloride (3182-93-2) → N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide (350027-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 95 percent / tetrahydrofuran / 1.5 h / -78 - -30 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0022-328X(00)00918-9

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → N-[1-benzyl-5,5-dimethoxy-2-oxo-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide (350027-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 95 percent / tetrahydrofuran / 1.5 h / -78 - -30 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0022-328X(00)00918-9

upstream raw materials:

(S)-ethyl 2-(4-methylphenylsulfonamido)-3-phenylpropanoate

1-(3,3-dimethoxypropylsulfonyl)-4-methylbenzene

(L)-phenylalanine ethyl ester hydrochloride

p-toluenesulfonyl chloride

Downstream raw materials:

Acetic acid (R)-4,4-dimethoxy-1-[(S)-2-phenyl-1-(toluene-4-sulfonylamino)-ethyl]-2-(toluene-4-sulfonyl)-butyl ester

Acetic acid (2S,3R)-2-benzyl-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridin-3-yl ester

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