pateamine A

Base Information

• Chemical Name: pateamine A
• CAS No.: 139220-18-1
• Molecular Formula: C31H45 N3 O4 S
• Molecular Weight: 555.782
• DSSTox Substance ID: DTXSID801098385
• Nikkaji Number: J943.653G
• Wikidata: Q104987951
• Metabolomics Workbench ID: 161191
• ChEMBL ID: CHEMBL1221966
• Mol file: 139220-18-1.mol

Synonyms:pateamine A

Chemical Property of pateamine A

Chemical Property:

• PSA: 122.99000
• LogP: 6.35700
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 555.31307810
• Heavy Atom Count: 39
• Complexity: 969

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(CC(=O)OC(CC(=CC=CC(=O)OC(CC2=NC1=CS2)C=C(C)C=CC(=CCN(C)C)C)C)C)N
• Isomeric SMILES: C[C@H]1C[C@H](CC(=O)O[C@H](C/C(=C/C=C\C(=O)O[C@@H](CC2=NC1=CS2)/C=C(\C)/C=C/C(=C/CN(C)C)/C)/C)C)N

Technology Process of pateamine A

There total 48 articles about pateamine A 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: 78.0%

C36H50Cl3N3O6S (201339-93-7) → (-)-pateamine (139220-18-1)

Guidance literature:

With 10% Cd/Pd; ammonium acetate; In tetrahydrofuran; at 25 ℃; for 3.5h;

DOI:10.1021/ja981846u

Reference yield:

tert-Butyl-((E)-(S)-4-iodo-1,3-dimethyl-but-3-enyloxy)-dimethyl-silane (218782-56-0) → (-)-pateamine (139220-18-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 94 percent / Pd(PPh₃)4, CuI, n-PrNH₂ / benzene / 20 h / 25 °C

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 20 min

3: 61 percent / H₂O₂, NaH₂PO₄, NaClO₂ / acetonitrile; 2-methyl-propan-2-ol / 2.5 h / 0 °C

4: 57 percent / DIAD, Ph₃P / tetrahydrofuran / 1.5 h / -20 °C

5: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C

6: 68 percent / Et₄NCN / CH₂Cl₂ / 6 h / 25 °C

7: H₂ / Pd/CaCO₃ poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr

8: 27 percent / Pd₂dba3*CHCl₃, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C

9: 78 percent / NH₄OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C

With pyridine; propylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium chlorite; sodium dihydrogenphosphate; 10% Cd/Pd; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; triphenyl-arsane; di-isopropyl azodicarboxylate; hydrogen fluoride; ammonium acetate; tetraethylammoniumcyanide; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1021/ja981846u

Reference yield:

(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oct-4-en-2-yn-1-ol (218782-58-2) → (-)-pateamine (139220-18-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 20 min

2: 61 percent / H₂O₂, NaH₂PO₄, NaClO₂ / acetonitrile; 2-methyl-propan-2-ol / 2.5 h / 0 °C

3: 57 percent / DIAD, Ph₃P / tetrahydrofuran / 1.5 h / -20 °C

4: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C

5: 68 percent / Et₄NCN / CH₂Cl₂ / 6 h / 25 °C

6: H₂ / Pd/CaCO₃ poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr

7: 27 percent / Pd₂dba3*CHCl₃, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C

8: 78 percent / NH₄OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium chlorite; sodium dihydrogenphosphate; 10% Cd/Pd; oxalyl dichloride; triphenyl-arsane; di-isopropyl azodicarboxylate; hydrogen fluoride; ammonium acetate; tetraethylammoniumcyanide; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja981846u

upstream raw materials:

C₃₆H₅₀Cl₃N₃O₆S

[(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1⁽²¹⁾,6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

((6Z,8E)-(3S,11S,15R,17S)-3-formyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1⁽²¹⁾,6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

((6Z,8E)-(3S,11S,15R,17S)-3-hydroxymethyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1⁽²¹⁾,6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

Refernces

• 1、 Remuinan,Pattenden. "Total synthesis of (-)-pateamine, a novel polyene bis-macrolide with immunosuppressive activity from the sponge Mycale sp.". . p. 7367 - 7371. Retrieved 2007/10/03.