(E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester

Base Information

• Chemical Name: (E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester
• CAS No.: 187872-01-1
• Molecular Formula: C₃₄H₅₁NO₅Si
• Molecular Weight: 581.868
• Mol file: 187872-01-1.mol

Synonyms:(E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester

Chemical Property of (E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester

There total 3 articles about (E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic 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: 78.0%

L-Isoleucin-tert-butylester (16874-08-1) + (E)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(toluene-4-sulfonyloxy)-hex-3-enoic acid methyl ester (187871-96-1) → (E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester (187872-01-1)

Guidance literature:

In tetrahydrofuran; at 80 ℃; for 120h;

DOI:10.1021/jm960553d

Reference yield:

(E)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hex-3-enoic acid methyl ester (187871-93-8) → (E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester (187872-01-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

2: 78 percent / tetrahydrofuran / 120 h / 80 °C

With dmap; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm960553d

Reference yield:

L-isoleucine tert-butyl ester hydrochloride (69320-89-4) + (E)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-oxo-hex-3-enoic acid methyl ester (160283-34-1) → (E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid methyl ester (187872-01-1)

Guidance literature:

With 3 A molecular sieve; sodium acetate; sodium cyanoborohydride; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm960553d

upstream raw materials:

L-Isoleucin-tert-butylester

(E)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(toluene-4-sulfonyloxy)-hex-3-enoic acid methyl ester

L-isoleucine tert-butyl ester hydrochloride

(E)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-oxo-hex-3-enoic acid methyl ester

Downstream raw materials:

(2S,3S)-2-[3-(4-Benzyloxy-benzyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

(2S,3S)-2-[5-Aminomethyl-3-(4-benzyloxy-benzyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

(2S,3S)-2-[5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-2,3,6,7-tetrahydro-azepin-1-yl]-3-methyl-pentanoic acid tert-butyl ester

(E)-6-((1S,2S)-1-tert-Butoxycarbonyl-2-methyl-butylamino)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hex-3-enoic acid