(S)-2-FMOC-AMINO-OCTANEDIOIC ACID 8-TERT-BUTYL ESTER

Base Information

• Chemical Name: (S)-2-FMOC-AMINO-OCTANEDIOIC ACID 8-TERT-BUTYL ESTER
• CAS No.: 276869-41-1
• Molecular Formula: C27H33NO6
• Molecular Weight: 467.562
• Hs Code.: 29225090
• Mol file: 276869-41-1.mol

Synonyms:(S)-2-(((9H-fluoren-9-yl)methyl9H-fluoren-9-yl)methoxy)carbonylamino)-8-tert-butoxy-8-oxooctanoic acid;(S)-Fmoc-2-amino-octanedioc acid-8-tert-butyl ester;Fmoc-Asu(OtBu);

Chemical Property of (S)-2-FMOC-AMINO-OCTANEDIOIC ACID 8-TERT-BUTYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.558
• Boiling Point: 633.79 °C at 760 mmHg
• PKA: 3.89±0.21(Predicted)
• Flash Point: 337.104 °C
• PSA: 101.93000
• Density: 1.184 g/cm³
• LogP: 5.66140
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Fmoc-asu(otbu)-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-FMOC-AMINO-OCTANEDIOIC ACID 8-TERT-BUTYL ESTER

There total 11 articles about (S)-2-FMOC-AMINO-OCTANEDIOIC ACID 8-TERT-BUTYL 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: 92.0%

2-(9H-fluoren-9-ylmethoxycarbonylamino)-oct-4-enedioic acid 1-benzyl ester 8-tert-butyl ester (868754-95-4) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-octanedioic acid 8-tert-butyl ester (276869-41-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h;

DOI:10.1021/ol0520222

Reference yield:

2-acetylamino-octanedioic acid 8-tert-butyl ester (853152-74-6) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-octanedioic acid 8-tert-butyl ester (276869-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH; acylase I from Aspergillus melleus / CoCl₂*6H₂O / aq. phosphate buffer / 48 h / 39 °C / pH 7.2

2: NaHCO₃ / tetrahydrofuran / 2 h

With sodium hydroxide; acylase I from Aspergillus melleus; sodium hydrogencarbonate; cobalt(II) chloride; In tetrahydrofuran; phosphate buffer;

DOI:10.1021/jm050214x

Reference yield:

2-acetylamino-octanedioic acid 8-tert-butyl ester 1-ethyl ester (853152-73-5) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-octanedioic acid 8-tert-butyl ester (276869-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / LiOH*H₂O / H₂O; ethanol / 1 h

2: aq. NaOH; acylase I from Aspergillus melleus / CoCl₂*6H₂O / aq. phosphate buffer / 48 h / 39 °C / pH 7.2

3: NaHCO₃ / tetrahydrofuran / 2 h

With lithium hydroxide; sodium hydroxide; acylase I from Aspergillus melleus; sodium hydrogencarbonate; cobalt(II) chloride; In tetrahydrofuran; phosphate buffer; ethanol; water;

DOI:10.1021/jm050214x

upstream raw materials:

2-(9H-fluoren-9-ylmethoxycarbonylamino)-oct-4-enedioic acid 1-benzyl ester 8-tert-butyl ester

2-amino-octanedioic acid 8-tert-butyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

2-acetylamino-octanedioic acid 8-tert-butyl ester

Downstream raw materials:

tert-butyl (7S)-7-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-8-oxo-8-[(2S)-2-(4-phenyl-1H-imidazol-2-yl)pyrrolidin-1-yl]octanoate

Refernces

• 1、 Ryan, Shannon J.,Zhang, Yongda,Kennan, Alan J.. "Convenient access to glutamic acid side chain homologues compatible with solid phase peptide synthesis". . p. 4765 - 4767. Retrieved 2007/10/03.