(+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXAMIDE

Base Information

• Chemical Name: (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXAMIDE
• CAS No.: 57207-22-4
• Molecular Formula: C16H28N4O10
• Molecular Weight: 436.41432
• Mol file: 57207-22-4.mol

Synonyms:N,N,N',N',N'',N'',12-Heptamethyl-1,4,7,10,13,16-hexaoxacyclooctad ecane-2,3,11-tricarboxamide;

Chemical Property of (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXAMIDE

Chemical Property:

• Melting Point: 183-190°C
• PSA: 116.31000
• LogP: -1.14150
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

(+)-(18-Crown-6)-2,3,11,12-tetracarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (+)-(18-Crown-6)-2,3,11,12-tetracarboxamide (cas# 57207-22-4) is a compound useful in organic synthesis.

Technology Process of (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXAMIDE

There total 5 articles about (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXAMIDE 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: 16.0%

N,N,N',N'-tetramethyl L-tartramide (26549-65-5) + diethylene glycol ditosylate (7460-82-4) → (2R,3R,11R,12R)-(+)-(N,N,N',N',N,N,N',N'-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxamide) (57207-22-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 80 ℃; for 8h;

Reference yield: 12.0%

2,2'-diiodoethyl ether (34270-90-1) + N,N,N',N'-tetramethyl L-tartramide (26549-65-5) → (2R,3R,11R,12R)-(+)-(N,N,N',N',N,N,N',N'-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxamide) (57207-22-4)

Guidance literature:

With thallium (I) ethoxide; In N,N-dimethyl-formamide;

Reference yield:

2,2'-diiodoethyl ether (34270-90-1) + N,N,N',N'-tetramethyl L-tartramide (26549-65-5) → (2R,3R,11R,12R)-(+)-(N,N,N',N',N,N,N',N'-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxamide) (57207-22-4) + (2R,3R,11R,12R,20R,21R)-(+)-N,N,N',N',N,N,N',N',N,N,N',N'-dodecamethyl-1,4,7,10,13,16,19,22,25-nonaoxacycloheptacosane-2,3,11,12,20,21-hexacarboxamide (77027-53-3)

Guidance literature:

With thallium (I) ethoxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) DMF, rt, 30 min, 2.) rt, 1 h; from rt to 70 deg C, 1 h; 70 deg C, 8 h;

DOI:10.1002/hlca.19800630736

upstream raw materials:

2,2'-diiodoethyl ether

N,N,N',N'-tetramethyl L-tartramide

diethylene glycol ditosylate

Downstream raw materials:

(2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid

Refernces

• 1、 Behr, Jean-Paul,Girodeau, Jean-Marc,Hayward, Rodney C.,Lehn, Jean-Marie,Sauvage, Jean-Pierre. "Molecular Receptors. Functionalized and Chiral Macrocyclic Polyethers Derived from Tartaric Acid". . p. 2096 - 2111. Retrieved 2007/10/02.