1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate

Base Information

Chemical Name:1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate
CAS No.:478920-11-5
Molecular Formula:C₂₆H₄₀N₂O₈Si
Molecular Weight:536.698
Hs Code.:

Synonyms:1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate

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Chemical Property of 1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate

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Technology Process of 1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate

There total 5 articles about 1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate 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: 65.0%

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 160579-23-7
methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate

: 478920-11-5
1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃;
DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield:

: 23632-67-9
(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

: 478920-11-5
1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 76 percent / SOCl₂ / Heating

2.1: 73 percent / LiAl(OtBu)3H / tetrahydrofuran / -78 °C

3.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

3.2: 76 percent / tetrahydrofuran / -78 - -30 °C

4.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

With thionyl chloride; potassium hexamethylsilazane; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; In tetrahydrofuran; 3.2: Wittig-Horner reaction;
DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield:

: 58456-26-1
(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

: 478920-11-5
1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 73 percent / LiAl(OtBu)3H / tetrahydrofuran / -78 °C

2.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

2.2: 76 percent / tetrahydrofuran / -78 - -30 °C

3.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

With potassium hexamethylsilazane; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; In tetrahydrofuran; 2.2: Wittig-Horner reaction;
DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8