Fmoc-suberol

Base Information

• Chemical Name: Fmoc-suberol
• CAS No.: 212783-75-0
• Molecular Formula: C₃₂H₂₇NO₅
• Molecular Weight: 505.57
• Hs Code.: 29062990
• European Community (EC) Number: 606-734-3
• DSSTox Substance ID: DTXSID901108676
• Nikkaji Number: J1.067.690H
• Mol file: 212783-75-0.mol

Synonyms:212783-75-0;FMOC-SUBEROL;Ramage Linker;2-((5-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-10,11-dihydro-5H-dibenzo[a,d][7]annulen-2-yl)oxy)acetic acid;Ramagelinker;Ramage-Linker;2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl]oxy]acetic acid;FMOC-SUBEROL, Ramage Linker;SCHEMBL22572694;DTXSID901108676;AMY22695;BCP16052;MFCD07783960;AKOS015920104;CS-W009750;AC-32003;CS-17334;FT-0643964;J-013969;5-Fmoc-Amino-10, 11-Dihydro-5H-Dibenzo[a,d]Cycloheptene-2-Hydroxy Acetic Acid;2-((5-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-10,11-dihydro-5H-dibenzo[a,d][7]annulen-2-yl)oxy)aceticacid;2-[[5-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yl]oxy]acetic acid;5-(9H-Fluorene-9-ylmethoxycarbonylamino)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-2-yloxyacetic acid;ACETIC ACID, 2-[[5-[[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO]-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-2-YL]OXY]-

Chemical Property of Fmoc-suberol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.697
• Boiling Point: 724.118 °C at 760 mmHg
• PKA: 3.22±0.10(Predicted)
• Flash Point: 391.732 °C
• PSA: 84.86000
• Density: 1.365 g/cm³
• LogP: 6.26760
• Storage Temp.: 2-8°C
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 505.18892296
• Heavy Atom Count: 38
• Complexity: 811

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-suberol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=CC(=C2)OCC(=O)O)C(C3=CC=CC=C31)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Uses: Fmoc-suberol, also known as Ramage-Linker can be used for preparation of peptide amides specially as a acid-labile peptide amide linker.

Technology Process of Fmoc-suberol

There total 8 articles about Fmoc-suberol 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:

9-fluorenylmethyl carbamate (84418-43-9) + 2-[(5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yl)oxy]acetic acid (229644-77-3) → 2-<<(R,S)-5-(Fmoc-amino)-10,11-dihydro-5H-dibenzocyclohepten-2-yl>oxy>acetic acid (212783-75-0)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 - 80 ℃; for 17.5h; Yield given;

DOI:10.1248/cpb.46.1157

Reference yield:

2-hydroxy-10,11-dihydro-5H-dibenzocyclohepten-5-one (17910-73-5) → 2-<<(R,S)-5-(Fmoc-amino)-10,11-dihydro-5H-dibenzocyclohepten-2-yl>oxy>acetic acid (212783-75-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) DMF, from 90 to 100 deg C, 4 h

2: 95 percent / 2N aq. NaOH / dioxane / 4 h / Ambient temperature

3: NaBH₄, Et₃N / propan-2-ol / 3 h / Heating

4: p-TsOH / dimethylformamide / 17.5 h / 20 - 80 °C

With sodium hydroxide; sodium tetrahydroborate; potassium tert-butylate; toluene-4-sulfonic acid; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1248/cpb.46.1157

Reference yield:

2-<(5-oxo-10,11-dihydro-5H-dibenzocyclohepten-2-yl)oxy>acetic acid (153645-42-2) → 2-<<(R,S)-5-(Fmoc-amino)-10,11-dihydro-5H-dibenzocyclohepten-2-yl>oxy>acetic acid (212783-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄, Et₃N / propan-2-ol / 3 h / Heating

2: p-TsOH / dimethylformamide / 17.5 h / 20 - 80 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; triethylamine; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1248/cpb.46.1157

upstream raw materials:

9-fluorenylmethyl carbamate

2-[(5-hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yl)oxy]acetic acid

2-hydroxy-10,11-dihydro-5H-dibenzocyclohepten-5-one

2-<(5-oxo-10,11-dihydro-5H-dibenzocyclohepten-2-yl)oxy>acetic acid

Refernces

• 1、 Noda, Masaki. "Facile synthesis of 3-methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten- 5-one: Application to the acid-labile peptide amide linker containing the 10,11-dihydro-5H-dibenzo[a,d]cycloheptene moiety". . p. 1157 - 1159. Retrieved 2007/10/03.