2-[(1R,9S,12S,13S,14S,17R,18E,21S,23S,24R,25R,27R)-14-[(tert-butyldimethylsilyl)oxy]-12-[(1E)-1-[(1R,3S,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexyl]prop-1-en-2-yl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en-17-yl]acetaldehyde

• ChemBase ID: 166395
• Molecular Formular: C55H95NO13Si2
• Molecular Mass: 1034.5127
• Monoisotopic Mass: 1033.63419517
• SMILES: [C@@H]1([C@H](C[C@@H](CC1)/C=C(/[C@@H]1[C@@H]([C@H](CC(=O)[C@@H](/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@@H](C[C@H]([C@](C(=O)C(=O)N3[C@H](C(=O)O1)CCCC3)(O2)O)C)OC)OC)C)\C)CC=O)O[Si](C(C)(C)C)(C)C)C)\C)OC)O[Si](C(C)(C)C)(C)C
• Canonical SMILES: O=CC[C@@H]1/C=C(\C)/C[C@H](C)C[C@H](OC)[C@H]2O[C@](O)([C@@H](C[C@H]2OC)C)C(=O)C(=O)N2[C@H](C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O[Si](C(C)(C)C)(C)C)C)/C(=C/[C@@H]1CC[C@H]([C@H](C1)OC)O[Si](C(C)(C)C)(C)C)/C)CCCC2
• InChI: InChI=1S/C55H95NO13Si2/c1-34-27-35(2)29-46(64-13)49-47(65-14)31-37(4)55(62,67-49)50(59)51(60)56-25-20-19-21-41(56)52(61)66-48(36(3)30-39-22-23-43(45(32-39)63-12)68-70(15,16)53(6,7)8)38(5)44(69-71(17,18)54(9,10)11)33-42(58)40(28-34)24-26-57/h26,28,30,35,37-41,43-49,62H,19-25,27,29,31-33H2,1-18H3/b34-28+,36-30+/t35-,37+,38+,39-,40+,41-,43+,44-,45-,46-,47+,48+,49?,55+/m0/s1
• InChIKey: KVRUABNQJVFBLO-TUJPEUQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,9S,12S,13S,14S,17R,18E,21S,23S,24R,25R,27R)-14-[(tert-butyldimethylsilyl)oxy]-12-[(1E)-1-[(1R,3S,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexyl]prop-1-en-2-yl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-azatricyclo[22.3.1.0^4,^9]octacos-18-en-17-yl]acetaldehyde
• IUPAC Traditional name: 2-[(1R,9S,12S,13S,14S,17R,18E,21S,23S,24R,25R,27R)-14-[(tert-butyldimethylsilyl)oxy]-12-[(1E)-1-[(1R,3S,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexyl]prop-1-en-2-yl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-azatricyclo[22.3.1.0^4,^9]octacos-18-en-17-yl]acetaldehyde
• Synonyms: 37-Desmethylene 24,33-Bis-O-(tert-butyldimethylsilyl)-37-oxo Tacrolimus; (3S,4S,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3-[(1E)-2-[(1R,3R,4R)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxycyclohexyl]-1-methylethenyl]-1,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,21,23,24,25,26,26a-docosahydro-19-hydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-1,7,20,21-tetraoxo-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-8-acetaldehyde; 37-Desmethylene 24,33-Bis-O-(tert-butyldimethylsilyl)-37-oxo-FK-506

Database IDs

• CAS Number: 155684-96-1
• PubChem SID: 162260528
• PubChem CID: 71315719

CALCULATED PROPERTIES

• Acid pKa: 9.955066
• H Acceptors: 12
• H Donor: 1
• LogD (pH = 5.5): 9.104085
• LogD (pH = 7.4): 9.102893
• Log P: 9.1041
• Molar Refractivity: 271.4114 cm^3
• Polarizability: 111.512436 Å^3
• Polar Surface Area: 173.43 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Pale Yellow Solid (Foam)

DETAILS

Toronto Research Chemicals - D291120

An intermediate in the preparation of labelled FK-506 (Tacrolimus)

REFERENCES

• Organ, H., et al.: Bioorg. Med. Chem. Lett., 3, 657 (1993)