Boc-S-4-methoxybenzyl-L-penicillamine

Base Information

• Chemical Name: Boc-S-4-methoxybenzyl-L-penicillamine
• CAS No.: 120944-75-4
• Molecular Formula: C18H27NO5S
• Molecular Weight: 369.482
• Hs Code.: 2922299090
• DSSTox Substance ID: DTXSID70427028
• Wikidata: Q82239792
• Mol file: 120944-75-4.mol

Synonyms:Boc-S-4-methoxybenzyl-L-penicillamine;Boc-Pen(Mob)-OH;120944-75-4;(R)-2-((tert-Butoxycarbonyl)amino)-3-((4-methoxybenzyl)thio)-3-methylbutanoic acid;(2R)-3-[(4-methoxyphenyl)methylsulfanyl]-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;Boc-Pen(MeOBzl)-OH;Boc-,-dimethyl-Cys(Mob)-OH;C18H27NO5S;SCHEMBL3151621;DTXSID70427028;MFCD00076975;AKOS025312283;HY-W141815;MS-25937;Boc-Pen(Mob)-OH, >=98.0% (TLC);CS-0201612;F82993;J-004418;(R)-2-(tert-butoxycarbonylamino)-3-(4-methoxybenzylthio)-3-methylbutanoic acid;L-Valine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(4-methoxyphenyl)methyl]thio]-

Chemical Property of Boc-S-4-methoxybenzyl-L-penicillamine

Chemical Property:

• Vapor Pressure: 8.95E-12mmHg at 25°C
• Melting Point: 108-115 °C
• Refractive Index: 1.538
• Boiling Point: 523.2 °C at 760 mmHg
• Flash Point: 270.2 °C
• PSA: 110.16000
• Density: 1.168 g/cm³
• LogP: 4.07580
• Storage Temp.: −20°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 369.16099414
• Heavy Atom Count: 25
• Complexity: 453

Purity/Quality:

97% ^*data from raw suppliers

Boc-S-4-methoxybenzyl-L-penicillamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C(=O)O)C(C)(C)SCC1=CC=C(C=C1)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C(=O)O)C(C)(C)SCC1=CC=C(C=C1)OC
• Uses: Boc-S-4-methoxybenzyl-L-penicillamine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Boc-S-4-methoxybenzyl-L-penicillamine

There total 3 articles about Boc-S-4-methoxybenzyl-L-penicillamine 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:

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-Amino-3-(4-methoxy-benzylsulfanyl)-3-methyl-butyric acid (387868-34-0) → N-tertbutyloxycarbonyl-S-p-methoxybenzyl-L-penicillamine (120944-75-4)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1016/j.bmcl.2004.05.077

Reference yield:

p-methoxybenzyl chloride (824-94-2) → N-tertbutyloxycarbonyl-S-p-methoxybenzyl-L-penicillamine (120944-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 72 h / 80 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / methanol / 3 h / Inert atmosphere; Reflux

With acetic acid; N-ethyl-N,N-diisopropylamine; In methanol;

DOI:10.3390/molecules191220751

Reference yield:

L-penicillamine (1113-41-3) → N-tertbutyloxycarbonyl-S-p-methoxybenzyl-L-penicillamine (120944-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 72 h / 80 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / methanol / 3 h / Inert atmosphere; Reflux

With acetic acid; N-ethyl-N,N-diisopropylamine; In methanol;

DOI:10.3390/molecules191220751

upstream raw materials:

di-tert-butyl dicarbonate

(R)-2-Amino-3-(4-methoxy-benzylsulfanyl)-3-methyl-butyric acid

p-methoxybenzyl chloride

L-penicillamine

Downstream raw materials:

Boc-Pen(MBzl)-Asn-Ser(Bzl)-Phe-Arg(Tos)-Tyr(BrZ)-OBzl

Boc-Pen(MBzl)-Phe-Gly-Gly-OPac

(E)-(S)-4-{[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-3-methyl-butyryl]-methyl-amino}-2,5-dimethyl-hex-2-enoic acid ethyl ester

(E)-(S)-4-{[(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-(4-methoxy-benzylsulfanyl)-3-methyl-butyryl]-methyl-amino}-2,5-dimethyl-hex-2-enoic acid