(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]-17-(2,3-dihydroxypropyl)-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

• ChemBase ID: 163309
• Molecular Formular: C56H99NO14Si2
• Molecular Mass: 1066.55456
• Monoisotopic Mass: 1065.66040992
• 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(CO)O)O[Si](C(C)(C)C)(C)C)C)\C)OC)O[Si](C(C)(C)C)(C)C
• Canonical SMILES: OCC(C[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)O
• InChI: InChI=1S/C56H99NO14Si2/c1-34-25-35(2)27-47(66-13)50-48(67-14)29-37(4)56(64,69-50)51(61)52(62)57-24-20-19-21-42(57)53(63)68-49(36(3)28-39-22-23-44(46(30-39)65-12)70-72(15,16)54(6,7)8)38(5)45(71-73(17,18)55(9,10)11)32-43(60)40(26-34)31-41(59)33-58/h26,28,35,37-42,44-50,58-59,64H,19-25,27,29-33H2,1-18H3/b34-26+,36-28+/t35-,37+,38+,39-,40-,41?,42-,44+,45-,46-,47-,48+,49+,50?,56+/m0/s1
• InChIKey: VVXLUGMPTYRRQJ-HQXPZUHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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]-17-(2,3-dihydroxypropyl)-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0^4,^9]octacos-18-ene-2,3,10,16-tetrone
• IUPAC Traditional name: (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]-17-(2,3-dihydroxypropyl)-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0^4,^9]octacos-18-ene-2,3,10,16-tetrone
• Synonyms: 24,33-Bis-O-(tert-butyldimethylsilyl)-37,38-dehydro-37,38-dihydroxy Tacrolimus; 24,33-Bis-O-(tert-butyldimethylsilyl)-37,38-dehydro-37,38-dihydroxy-FK-506 (mixture of diastereomers)

Database IDs

• CAS Number: 1356932-17-6
• PubChem SID: 162257444
• PubChem CID: 71314379

CALCULATED PROPERTIES

• Acid pKa: 9.955422
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 8.628885
• LogD (pH = 7.4): 8.627694
• Log P: 8.6289
• Molar Refractivity: 278.5626 cm^3
• Polarizability: 114.535034 Å^3
• Polar Surface Area: 196.82 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Light Grey Solid
• Melting Point: 125-127°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B691090

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