(1R,8S,11S,12S,13S,16R,17E,20S,22S,23R,24R,26R)-1-hydroxy-11-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-22,24-dimethoxy-12,18,20,26-tetramethyl-16-(prop-2-en-1-yl)-13-{[tris(propan-2-yl)silyl]oxy}-10,27-dioxa-3-azatricyclo[21.3.1.03,8]heptacos-17-ene-2,9,15-trione

• ChemBase ID: 179159
• Molecular Formular: C52H89NO11Si
• Molecular Mass: 932.34866
• Monoisotopic Mass: 931.62048921
• 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@](O2)(O)C(=O)N2[C@H](C(=O)O1)CCCC2)C)OC)OC)C)\C)CC=C)O[Si](C(C)C)(C(C)C)C(C)C)C)\C)OC)O
• Canonical SMILES: C=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)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)/C(=C/[C@@H]1CC[C@H]([C@H](C1)OC)O)/C)CCCC2
• InChI: InChI=1S/C52H89NO11Si/c1-16-19-40-25-34(8)24-35(9)26-46(60-14)49-47(61-15)28-37(11)52(58,63-49)51(57)53-23-18-17-20-41(53)50(56)62-48(36(10)27-39-21-22-42(54)45(29-39)59-13)38(12)44(30-43(40)55)64-65(31(2)3,32(4)5)33(6)7/h16,25,27,31-33,35,37-42,44-49,54,58H,1,17-24,26,28-30H2,2-15H3/b34-25+,36-27+/t35-,37+,38+,39-,40+,41-,42+,44-,45-,46-,47+,48+,49?,52+/m0/s1
• InChIKey: QOPPKWCRXKAHTN-VEMDLOSMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,8S,11S,12S,13S,16R,17E,20S,22S,23R,24R,26R)-1-hydroxy-11-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-22,24-dimethoxy-12,18,20,26-tetramethyl-16-(prop-2-en-1-yl)-13-{[tris(propan-2-yl)silyl]oxy}-10,27-dioxa-3-azatricyclo[21.3.1.0^3,^8]heptacos-17-ene-2,9,15-trione
• IUPAC Traditional name: (1R,8S,11S,12S,13S,16R,17E,20S,22S,23R,24R,26R)-1-hydroxy-11-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-22,24-dimethoxy-12,18,20,26-tetramethyl-16-(prop-2-en-1-yl)-13-[(triisopropylsilyl)oxy]-10,27-dioxa-3-azatricyclo[21.3.1.0^3,^8]heptacos-17-ene-2,9,15-trione
• Synonyms: [3S-[3R*[E(1S*,3S*,4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,25aR*]]- 3,4,5,6,8,11,12,13,14,15,16,17,18,19,23,24,25,25a-Octadecahydro-5-O-Triisopropylsilyl-19-hydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-15,19-epoxypyrido[2,1-c][1,4]oxaazacyclodocosine-1,7,20(22H)-trione; 24-O-Triisopropylsilyl 9-Norketo FK-506

Database IDs

• PubChem SID: 164235069
• PubChem CID: 71752798

CALCULATED PROPERTIES

• Acid pKa: 9.918655
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): 8.919483
• LogD (pH = 7.4): 8.918187
• Log P: 8.9195
• Molar Refractivity: 253.7356 cm^3
• Polarizability: 102.55841 Å^3
• Polar Surface Area: 150.29 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Colorless Oil

DETAILS

Toronto Research Chemicals - T795540

Protected FK-506 (F370000) impurity. A FK-506 derivative prepared via base-mediated FK-506 rearrangement and oxidation.

REFERENCES

• Askin, D., et al.: Tetrahedron Lett., 30, 671 (1989)