(R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid

Base Information

• Chemical Name: (R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid
• CAS No.: 937242-43-8
• Molecular Formula: C₂₁H₃₄N₂O₇Si
• Molecular Weight: 454.596
• Mol file: 937242-43-8.mol

Synonyms:(R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid

Chemical Property of (R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid

There total 6 articles about (R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic 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: 90.0%

Nα-Cbz-Nε-formyl-Nε-[[2-(trimethylsilyl)ethoxy]methoxy]-D-lysine methyl ester (284469-96-1) → (R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid (937242-43-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2007.09.112

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → (R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid (937242-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DIPEA; DMAP / CH₂Cl₂ / 17.5 h / 0 - 20 °C

2: aq. LiOH / tetrahydrofuran / 1.5 h / 0 - 20 °C

With dmap; lithium hydroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Condensation / 2: Hydrolysis;

DOI:10.1016/S0040-4020(00)00170-8

Reference yield:

(R)-2-Benzyloxycarbonylamino-6-hydroxyamino-hexanoic acid methyl ester → (R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid (937242-43-8)

Guidance literature:

Multi-step reaction with 4 steps

1: EDCI*HCl; NH₂OH / CH₂Cl₂ / 0 °C

2: DIPEA / methanol / 62 h / 20 °C

3: 92 percent / DIPEA; DMAP / CH₂Cl₂ / 17.5 h / 0 - 20 °C

4: aq. LiOH / tetrahydrofuran / 1.5 h / 0 - 20 °C

With dmap; lithium hydroxide; hydroxylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 1: Acylation / 2: Hydrolysis / 3: Condensation / 4: Hydrolysis;

DOI:10.1016/S0040-4020(00)00170-8

upstream raw materials:

N^α-Cbz-N^ε-formyl-N^ε-[[2-(trimethylsilyl)ethoxy]methoxy]-D-lysine methyl ester

(2-trimethylethylsilylethoxy)methyl chloride

N^α-Cbz-N^ε-hydroxy-N^ε-formyl-D-lysine methyl ester

C₁₈H₂₆N₂O₅

Downstream raw materials:

(R)-2-Benzyloxycarbonylamino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid (S)-1-{1-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-2-{[2-(2-hydroxy-5-methoxy-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-hexanoic acid 1-{1-[1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

(R)-2-Amino-6-[formyl-(2-trimethylsilanyl-ethoxymethoxy)-amino]-hexanoic acid (S)-1-{1-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-ylcarbamoyl]-1-methyl-ethyl}-octyl ester

amamistatin A