4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid

Base Information

• Chemical Name: 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid
• CAS No.: 592532-21-3
• Molecular Formula: C₂₇H₃₉NO₅Si
• Molecular Weight: 485.696

Synonyms:4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid

Chemical Property of 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid

Chemical Property:

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Technology Process of 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid

There total 1 articles about 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid 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:

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (138871-61-1) → 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid (592532-21-3)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; at 0 ℃; for 3h;

DOI:10.1021/ol035125y

Reference yield: 83.0%

benzyl bromide (100-39-0) + 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid (592532-21-3) → 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid benzyl ester (592532-22-4)

Guidance literature:

With caesium carbonate; In acetone; at 30 ℃; for 1h;

DOI:10.1021/ol035125y

Reference yield:

4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid (592532-21-3) → (2R,4S)-4-tert-Butoxycarbonylamino-5-hydroxy-2-methyl-pentanoic acid benzyl ester (592532-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / Cs₂CO₃ / acetone / 1 h / 30 °C

2: 85 percent / aq. AcOH; TBAF / tetrahydrofuran / 0 - 20 °C

With tetrabutyl ammonium fluoride; caesium carbonate; acetic acid; In tetrahydrofuran; acetone;

DOI:10.1021/ol035125y

upstream raw materials:

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid benzyl ester

methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate

(2R,4S)-4-tert-Butoxycarbonylamino-5-hydroxy-2-methyl-pentanoic acid benzyl ester

(2S,4R)-2-tert-Butoxycarbonylamino-4-methyl-pentanedioic acid 5-benzyl ester

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