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

Base Information

• Chemical Name: 4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid benzyl ester
• CAS No.: 592532-22-4
• Molecular Formula: C₃₄H₄₅NO₅Si
• Molecular Weight: 575.821

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

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

Chemical Property:

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

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

(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 benzyl ester (592532-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. LiOH / dioxane / 3 h / 0 °C

2: 83 percent / Cs₂CO₃ / acetone / 1 h / 30 °C

With lithium hydroxide; caesium carbonate; In 1,4-dioxane; acetone;

DOI:10.1021/ol035125y

Reference yield: 85.0%

4-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pentanoic acid benzyl ester (592532-22-4) → (2R,4S)-4-tert-Butoxycarbonylamino-5-hydroxy-2-methyl-pentanoic acid benzyl ester (592532-50-8)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol035125y

upstream raw materials:

benzyl bromide

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

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

Downstream raw materials:

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

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

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

(2S,4R)-2-tert-Butoxycarbonylamino-4-methyl-pentanedioic acid 5-benzyl ester 1-methyl ester

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