Alternative syntheses of (S)-cEt-BNA: A key constrained nucleoside component of bioactive antisense gapmer sequences

Journal of Organic Chemistry

Volumn 79, Issue 23, 2014, Pages 11651-11660

  Salinas, Juan C ^a   Migawa, Michael T ^b   Merner, Bradley L ^a   Hanessian, Stephen ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; OLIGONUCLEOTIDES; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

ALTERNATIVE SYNTHESIS; ANTISENSE; ANTISENSE OLIGONUCLEOTIDES; INTRAMOLECULAR CYCLIZATIONS; LINEAR SEQUENCE; OXETANES;

CYCLIZATION;

1 [ 1 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 4 HYDROXY 7 METHYL 2,6 DIOXABICYCLO[3.2.0]HEPTAN 3 YL] 5 METHYLPYRIMIDINE 2,4(1H,3H) DIONE; 1 [ 2 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 3,4 DIHYDROXY 5 [5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] TETRAHYDROFURAN 2 YL] ETHYL METHANESULFONATE; 1 [ 4 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 6 [5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 2 PHENYLTETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL]ETHYL METHANESULFATE; 1 [ 4' [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 4' (1 HYDROXYETHYL)TETRAHYDROSPIRO[CYCLOHEXANE 1,2' FURO[3,4 D][1,3]DIOXOL] 6' YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [ 4' [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 4' (HYDROXYMETHYL)TETRAHYDROSPIRO[CYCLOHEXANE 1,2' FURO[3,4 D][1,3]DIOXOL] 6' YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [ 7 (BENZYLOXY) 1 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 6 METHYL 2,5 DIOXABICYCLO[2.2.1]HEPTAN 3 YL] 5 METHYLPYRIMIDINE 2,4(1H,3H) DIONE; 1 [1 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 6 METHYL 7 (NAPHTHALEN 2 YLMETHOXY) 2,5 DIOXABICYCLO[2.2.1] HEPTAN 3 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [1 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 7 HYDROXY 6 METHYL 2,5 DIOXABICLO[2.2.1]HEPTAN 3 YL] 5 METHYLPYRIMIDINE 2,4(1H,3H) DIONE; 1 [2 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 3,4 DIHYDROXY 5 [5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H YL]TETRAHYDROFURAN 2 YL]ETHYL 4 METHYLBENZENESULFONATE; 1 [3 HYDROXY 5 (HYDROXYMETHYL) 4 (NAPHTHALEN 2 YLMETHOXY)TETRAHYDROFURAN 2 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [3 [(TERT BUTYLDIMETHYLSILYL)OXY] 5 HYDROXY (HYDROXYMETHYL) 4 (NAPHTHALEN 2 YLMETHOXY)TETRAHYDROFURAN 2 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [3 [(TERT BUTYLDIMETHYLSILYL)OXY] 5 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 5 (1 HYDROXYETHYL) 4 (NAPHTHALEN 2 YLMETHOXY)TETRAHYDROFURAN 2 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [3 [(TERT BUTYLDIMETHYLSILYL)OXY] 5 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 5 (HYDROXYMETHYL) 4 (NAPHTHALEN 2 YLMETHOXY)TETRAHYDROFURAN 2 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [3 [(TERT BUTYLDIMETHYLSILYL)OXY] 5,5 BIS (HYDROXYMETHYL) 4 (NAPHTHALEN 2 YLMETHOXY)TETRAHYDROFURAN 2 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; 1 [4 [(TERT BUTYLDIMETHYLSILYL)OXY] 2 [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 5 [5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 3 (NAPHTHALEN 2 YLMETHOXY)TETRAHYDROFURAN 2 YL]ETHYL METHANESULFATE; 1 [4' [[(TERT BUTYLDIPHENYLSILYL)OXY]METHYL] 6' [5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL] TETRAHYDROSPIRO[CYCLOHEZANE 1,2' FURO[3,4 D][1,3]DIOXOL] 4'YL]ETHYL 4 METHYLBENZENESULFONATE; 1 [6 (HYDROXYMETHYL) 2 (NAPHTHALEN 2 YL)TETRAHYDROFURO[3,4 D][1,3]DIOXOL 4 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H) DIONE; ALDEHYDE; ANTISENSE OLIGONUCLEOTIDE; CYCLOHEPTANE DERIVATIVE; NUCLEOSIDE DERIVATIVE; OXETANE DERIVATIVE; UNCLASSIFIED DRUG; BICYCLO COMPOUND; BRIDGED COMPOUND; ETHER DERIVATIVE; NUCLEOSIDE; OXETANE; THYMINE; URIDINE;

ALDOL REACTION; ARTICLE; CROSS ALDOL REACTION; CYCLIZATION; DRUG SYNTHESIS; HYDROGENOLYSIS; INTRAMOLECULAR CYCLIZATION; OXIDATION REDUCTION REACTION; REACTION TIME; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BICYCLO COMPOUNDS; BRIDGED COMPOUNDS; CYCLIZATION; ETHERS, CYCLIC; MOLECULAR STRUCTURE; NUCLEOSIDES; OLIGONUCLEOTIDES, ANTISENSE; THYMINE; URIDINE;

EID: 84916208208     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502320y     Document Type: Article

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