5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester

Base Information

• Chemical Name: 5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester
• CAS No.: 444616-35-7
• Molecular Formula: C₂₉H₄₂N₂O₇Si
• Molecular Weight: 558.747

Synonyms:5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester

Chemical Property of 5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester

Chemical Property:

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Technology Process of 5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester

There total 5 articles about 5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester 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%

sodium methylate (124-41-4) + 2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitromethyl-6-oxo-piperidine-1-carboxylic acid tert-butyl ester (444615-87-6) → 5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester (444616-35-7)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00183-1

Reference yield:

tert-butyl (2S)-2-(hydroxymethyl)piperidine-1-carboxylate (134441-93-3) → 5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester (444616-35-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DMAP / CH₂Cl₂

1.2: 80 percent / RuO₂*H₂O; NaIO₄ / H₂O; ethyl acetate

2.1: LiHMDS; PhSeBr / tetrahydrofuran

2.2: 75 percent / H₂O₂ / pyridine; CH₂Cl₂

3.1: 50 percent Turnov_. / DBU

4.1: 95 percent / tetrahydrofuran

With dmap; Phenylselenyl bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(02)00183-1

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-3-nitromethyl-hexanoic acid methyl ester (444616-35-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DMAP / CH₂Cl₂

1.2: 80 percent / RuO₂*H₂O; NaIO₄ / H₂O; ethyl acetate

2.1: LiHMDS; PhSeBr / tetrahydrofuran

2.2: 75 percent / H₂O₂ / pyridine; CH₂Cl₂

3.1: 50 percent Turnov_. / DBU

4.1: 95 percent / tetrahydrofuran

With dmap; Phenylselenyl bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(02)00183-1

upstream raw materials:

sodium methylate

2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitromethyl-6-oxo-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl (2S)-2-(hydroxymethyl)piperidine-1-carboxylate

tert-butylchlorodiphenylsilane

Downstream raw materials:

[2-(tert-butyl-diphenyl-silanyloxy)-1-(5-oxo-pyrrolidin-3-ylmethyl)-ethyl]-carbamic acid tert-butyl ester

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