methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate

Base Information

Chemical Name:methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate
CAS No.:819868-08-1
Molecular Formula:C₂₃H₃₅NO₅SSi
Molecular Weight:465.686
Hs Code.:

Synonyms:methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate

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Chemical Property of methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate

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Technology Process of methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate

There total 3 articles about methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate 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: 75.0%

: 79-22-1
methyl chloroformate

: 819868-07-0
1-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-3-yne

: 819868-08-1
methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate

Guidance literature:: 1-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-3-yne; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

methyl chloroformate; In tetrahydrofuran; at -78 - 20 ℃; for 1h;
DOI:10.1021/ja046824o

Reference yield:

: 161040-05-7
N-(but-3-yn-1-yl)-4-methylbenzenesulfonamide

: 819868-08-1
methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / (η³-C3H5PdCl)2; Ph3P; Cs2CO3 / tetrahydrofuran / 1 h / 60 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 75 percent / tetrahydrofuran / 1 h / -78 - 20 °C

With n-butyllithium; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; triphenylphosphine; In tetrahydrofuran;
DOI:10.1021/ja046824o

Reference yield:

: 194301-35-4
Carbonic acid (Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl ester methyl ester

: 819868-08-1
methyl 5-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]pent-2-ynoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / (η³-C3H5PdCl)2; Ph3P; Cs2CO3 / tetrahydrofuran / 1 h / 60 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 75 percent / tetrahydrofuran / 1 h / -78 - 20 °C

With n-butyllithium; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; triphenylphosphine; In tetrahydrofuran;
DOI:10.1021/ja046824o