Diastereoselective addition of planar N-heterocycles to vinyl sulfone-modified carbohydrates: a new route to isonucleosides

Tetrahedron

Volumn 64, Issue 45, 2008, Pages 10406-10416

  Sanki, Aditya K ^a   Bhattacharya, Rahul ^b   Atta, Ananta Kumar ^b   Suresh, Cheravakkattu G ^a   Pathak, Tanmaya ^b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

METHYL 2 C (ADENIN 9 YL) 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2 C (N ACETYL ADENIN 9 YL) 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2 C (N ACETYL ADENIN 9 YL) 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE)ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2 C ADENIN 9 YL 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) 3 C PHENYLSULFONYL ALPHA DEXTRO GLUCOPYRANOSIDE DERIVATIVE; METHYL 2 C ADENIN 9 YL 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) 3 C PHENYLSULFONYL BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2 C ADENIN 9 YL 5 O BENZYL 2,3 DIDEOXY 3 C 4 TOLUENESULFONYL ALPH DEXTRO ARABINOFURANOSIDE; METHYL 2 C ADENIN 9 YL 5 O BENZYL 2,3 DIDEOXY 3 C 4 TOLUENESULFONYL BETA DEXTRO RIBOFURANOSIDE; METHYL 2,3 DIDEOXY 2 C IMIDAZOLYL 4,6 O (PHENYLMETHYLENE) 3 C PHENYLFULFONYL ALPHA DEXTROMANNOPYRANOSIDE; METHYL 2,3 DIDEOXY 2 C IMIDAZOLYL 4,6 O (PHENYLMETHYLENE) 3 C PHENYLSULFONYL BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 3 C 4 TOLUENESULFONYL 6 O TRITYL ALPHA DEXTRO ERYTHRO HEX 2 ENOPYRANOSIDE; METHYL 2,3 DIDEOXY 3 C 4 TOLUENESULFONYL 6 O TRITYL BETA DEXTRO ERYTHRO HEX 2 ENOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 DI O ACETYL 2 C ( N ACETYL ADENIN 9 YL) BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 DI O ACETYL 2 C (N ACETYL ADENIN 9 YL) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 DI O ACETYL 2 C (THYMIN 1 YL) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 DI O ACETYL 2 C (THYMIN 1 YL) BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) 3 C 4 TOLUENESULFONYL BETA DEXTRO ERYTHRO HEX 2 ENOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) 3 C PHENYLSULFONYL 2 C (1H 1,2,4 TRIAZOL 1 YL) ALPHA DEXTRO MANNOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) 3 C PHENYLSULFONYL 2 C (1H 1,2,4 TRIAZOL 1 YL) BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) 3 C PHENYLSULFONYL 2 C (THYMIN 1 YL) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 4,6 O (PHENYLMETHYLENE) 3 C PHENYLSULFONYL 2 C (THYMIN 1 YL) BETA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 6 O TRITYL 2 C (ADENIN 9 YL) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DIDEOXY 6 O TRITYL 2 C 9ADENIN 9 YL) BETA DEXTRO GLUCOPYRANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 C (THYMIN 1 YL) 3 C 4 TOLUENESULFONYL BETA DEXTRO XYLOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 C IMIDAZOLYL 3 C 4 TOLUENESULFONYL ALPHA DEXTRO ARABINOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 C IMIDAZOLYL 3 C 4 TOLUENESULFONYL BETA DEXTRO RIBOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 2 C THYMIN 1 YL 3 C 4 TOLUENESULFONYL ALPHA DEXTRO ARABINOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 3 C 4 TOLUENESULFONYL 2 C (1H 1,2,4 TRIAZOL 1 YL) ALPHA DEXTRO ARABINOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 3 C 4 TOLUENESULFONYL 2 C (1H 1,2,4 TRIAZOL 1 YL) BETA DEXTRO RIBOFURANOSIDE; METHYL 5 O BENZYL 2,3 DIDEOXY 3 C 4 TOLUENESULFONYL 2 C (1H 1,2,4 TRIAZOL 1 YL) BETA DEXTRO XYLOFURANOSIDE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CRYSTAL STRUCTURE; DEPROTECTION REACTION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 52049094829     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.050     Document Type: Article

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96. Desulfonylated nucleosides were isolated as peracetylated derivatives 25, 26, 37, and 40 for their easy isolation and characterization. For further modifications these compounds may be deacetylated and reprotected. Alternatively, compounds 5 and 9, immediately after desulfonylation and debenzyledination (Scheme 7) may be protected with other masking groups and isolated. For adenine analogues, the tritylated compounds 39 (Scheme 10) and 36 (Scheme 11) may be functionalized directly depending on the requirement.