L-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl-1,3-dithian-2-yl)meth yl ester

Base Information

• Chemical Name: L-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl-1,3-dithian-2-yl)meth yl ester
• CAS No.: 398142-91-1
• Molecular Formula: C42H45NO8S2
• Molecular Weight: 755.953
• Mol file: 398142-91-1.mol

Synonyms:

Chemical Property of L-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl-1,3-dithian-2-yl)meth yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl-1,3-dithian-2-yl)meth yl ester

There total 9 articles about L-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl-1,3-dithian-2-yl)meth yl 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: 70.0%

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyric acid [3-(3-tert-butoxycarbonylpropoxy)-5-methoxyphenyl](2-phenyl[1,3]dithian-2-yl)methyl ester (398142-90-0) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyric acid [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl[1,3]dithian-2-yl)methyl ester (398142-91-1)

Guidance literature:

With formic acid; at 20 ℃; for 6h;

DOI:10.1021/jo010703e

Reference yield:

2-Phenyl-[1,3]dithiane (5425-44-5) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyric acid [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl[1,3]dithian-2-yl)methyl ester (398142-91-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / 0 °C

1.2: tetrahydrofuran / 2.5 h / 20 °C

1.3: 80 percent / pyridine / tetrahydrofuran / 0.5 h

2.1: 81 percent / HF*pyr / tetrahydrofuran / 0 °C

3.1: 75 percent / tetrabutylammonium iodide; K₂CO₃ / acetonitrile / 20 h / 90 °C

4.1: 95 percent / K₂CO₃; Et₃N / methanol; H₂O / 3 h / 70 °C

5.1: 90 percent / PS-carbodiimide resin; DMAP / CH₂Cl₂ / 5 h / 20 °C

6.1: 70 percent / HCO₂H / 6 h / 20 °C

With dmap; n-butyllithium; formic acid; PS-carbodiimide resin; tetra-(n-butyl)ammonium iodide; potassium carbonate; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo010703e

Reference yield:

3-hydroxy-5-methoxybenzaldehyde (57179-35-8) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyric acid [3-(3-carboxypropoxy)-5-methoxyphenyl](2-phenyl[1,3]dithian-2-yl)methyl ester (398142-91-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / DIPEA / CH₂Cl₂; diethyl ether / 24 h

2.1: n-BuLi / tetrahydrofuran / 1 h / 0 °C

2.2: tetrahydrofuran / 2.5 h / 20 °C

2.3: 80 percent / pyridine / tetrahydrofuran / 0.5 h

3.1: 81 percent / HF*pyr / tetrahydrofuran / 0 °C

4.1: 75 percent / tetrabutylammonium iodide; K₂CO₃ / acetonitrile / 20 h / 90 °C

5.1: 95 percent / K₂CO₃; Et₃N / methanol; H₂O / 3 h / 70 °C

6.1: 90 percent / PS-carbodiimide resin; DMAP / CH₂Cl₂ / 5 h / 20 °C

7.1: 70 percent / HCO₂H / 6 h / 20 °C

With dmap; n-butyllithium; formic acid; PS-carbodiimide resin; tetra-(n-butyl)ammonium iodide; potassium carbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/jo010703e

upstream raw materials:

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutyric acid [3-(3-tert-butoxycarbonylpropoxy)-5-methoxyphenyl](2-phenyl[1,3]dithian-2-yl)methyl ester

2-Phenyl-[1,3]dithiane

3-hydroxy-5-methoxybenzaldehyde

Fmoc-Val-OH