1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate

Base Information

• Chemical Name: 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate
• CAS No.: 922706-06-7
• Molecular Formula: C₂₇H₃₂N₂O₆
• Molecular Weight: 480.561
• Mol file: 922706-06-7.mol

Synonyms:

Chemical Property of 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate

There total 6 articles about 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate 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: 45.0%

phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate (922705-76-8) + tert-butyl alcohol (75-65-0) → 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate (922706-06-7)

Guidance literature:

silver trifluoroacetate; In 1,4-dioxane; for 0.5h; sonication;

DOI:10.1002/hlca.200690235

Reference yield: 43.0%

(3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid (922705-78-0) + tert-butyl alcohol (75-65-0) → 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate (922706-06-7)

Guidance literature:

With dmap; di-tert-butyl dicarbonate; at 20 ℃; for 20h;

DOI:10.1002/hlca.200690235

Reference yield:

Cbz-Orn(NPhth)-OH (7767-00-2) → 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate (922706-06-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 70 percent / CSA / toluene / Heating

2.1: 63 percent / Et₃SiH; CF₃COOH / CH₂Cl₂

3.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C

3.2: 53 percent / tetrahydrofuran; CH₂Cl₂ / -15 - 20 °C

4.1: 72 percent / CF₃COOAg / dioxane; H₂O / 0.5 h / sonication

5.1: 43 percent / DMAP; Boc₂O / 20 h / 20 °C

With 4-methyl-morpholine; triethylsilane; dmap; di-tert-butyl dicarbonate; silver trifluoroacetate; chloroformic acid ethyl ester; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 4.1: Wolff rearrangement;

DOI:10.1002/hlca.200690235

upstream raw materials:

phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate

tert-butyl alcohol

(3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid

phenylmethyl (4S)-4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-5-oxo-1,3-oxazolidine-3-carboxylate