Tacrolimus Impurity 2

Base Information

• Chemical Name: Tacrolimus Impurity 2
• CAS No.: 131944-48-4
• Molecular Formula: C₄₄H₆₉NO₁₂
• Molecular Weight: 804.031
• UNII: Y8RY7CLE8L
• Mol file: 131944-48-4.mol

Synonyms:Tacrolimus Impurity 2;Y8RY7CLE8L;FK506-a;UNII-Y8RY7CLE8L;131944-48-4;(E/Z)-FK-506 26,28-Allylic Ester Rearrangement Impurity;17,21-EPOXY-3H-PYRIDO(2,1-C)(1,4)OXAAZACYCLOPENTACOSINE-1,9,22,23(6H,25H)-TETRONE, 7,8,10,13,14,15,16,17,18,19,20,21,26,27,28,28A-HEXADECAHYDRO-7,21-DIHYDROXY-3-(4-HYDROXY-3-METHOXYCYCLOHEXYL)-16,18-DIMETHOXY-4,6,12,14,20-PENTAMETHYL-10-(2-PROPENYL)-, (3R-(3R*(1R*,3R*,4R*),4E,6S*,7S*,10R*,11E,14S*,16S*,17R*,18S*,20R*,21R*,28AS*))-

Chemical Property of Tacrolimus Impurity 2

Chemical Property:

• Melting Point: 115-120°C
• Boiling Point: 879.7±75.0 °C(Predicted)
• PKA: 9.98±0.70(Predicted)
• PSA: 178.36000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 4.57690
• Storage Temp.: -20?C Freezer
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 803.48197664
• Heavy Atom Count: 57
• Complexity: 1480

Purity/Quality:

99% ^*data from raw suppliers

(E/Z)-FK-50626,28-AllylicEsterRearrangementImpurity ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(=CC(C(CC(=O)C(C=C(C1)C)CC=C)O)C)C)C4CCC(C(C4)OC)O)O)C)OC)OC
• Isomeric SMILES: C[C@@H]1C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H](/C(=C/[C@@H]([C@H](CC(=O)[C@@H](/C=C(/C1)\C)CC=C)O)C)/C)[C@@H]4CC[C@H]([C@@H](C4)OC)O)O)C)OC)OC
• Uses: FK-506 (F370000) impurity. A new macrolite of thermal rearrangement of the immunosuppressant FK-506.

Technology Process of Tacrolimus Impurity 2

There total 1 articles about Tacrolimus Impurity 2 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: 45.0%

(3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone (104987-11-3,129212-35-7,135635-56-2,144490-63-1) → (13E,20E)-(1R,9S,12R,15S,16S,19S,23S,25S,26R,27S,29R)-19-Allyl-1,16-dihydroxy-12-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-25,27-dimethoxy-13,15,21,23,29-pentamethyl-11,30-dioxa-4-aza-tricyclo[24.3.1.04,9]triaconta-13,20-diene-2,3,10,18-tetraone (131944-48-4)

Guidance literature:

In xylene; for 24h; Heating;

DOI:10.1016/S0040-4039(00)97095-3

Reference yield:

(13E,20E)-(1R,9S,12R,15S,16S,19S,23S,25S,26R,27S,29R)-19-Allyl-1,16-dihydroxy-12-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-25,27-dimethoxy-13,15,21,23,29-pentamethyl-11,30-dioxa-4-aza-tricyclo[24.3.1.04,9]triaconta-13,20-diene-2,3,10,18-tetraone (131944-48-4) → (13E,16E,20E)-(1R,9S,12R,15R,19S,23S,25S,26R,27S,29R)-19-Allyl-1-hydroxy-12-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-25,27-dimethoxy-13,15,21,23,29-pentamethyl-11,30-dioxa-4-aza-tricyclo[24.3.1.04,9]triaconta-13,16,20-triene-2,3,10,18-tetraone (131944-49-5)

Guidance literature:

In xylene; Heating;

DOI:10.1016/S0040-4039(00)97095-3

upstream raw materials:

(3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone

Downstream raw materials:

(13E,16E,20E)-(1R,9S,12R,15R,19S,23S,25S,26R,27S,29R)-19-Allyl-1-hydroxy-12-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-25,27-dimethoxy-13,15,21,23,29-pentamethyl-11,30-dioxa-4-aza-tricyclo[24.3.1.0^4,9]triaconta-13,16,20-triene-2,3,10,18-tetraone

Refernces