e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A highly stereoselective synthesis of anti-HIV 2', 3'-dideoxy-and 2', 3'-didehydro-2', 3'-dideoxynucleosides

JW Beach, HO Kim, LS Jeong, S Nampalli…

Index: Beach, J. Warren; Kim, Hea O.; Jeong, Lak S.; Nampalli, Satyanarayana; Islam, Qamrul; et al. Journal of Organic Chemistry, 1992 , vol. 57, # 14 p. 3887 - 3894

Full Text: HTML

Citation Number: 87

Abstract

A general total synthetic method for the stereocontrolled synthesis of 2', 3 '-dideoxy-as well as 2 ', 3'-di-dehydro-2', 3'-dideoxynucleosidea is presented. Introduction of an a- phenylselenenyl group at the 2-position of 2, 3-dideoryriboeyl acetate directs the glycosyl bond formation to give 295% &isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2', 3'-dideoxynucleoside by treatment with n-Bu3SnH and E@ at ...

N6-methyl-9-(5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine Structure

N6-methyl-9-(5-...

~90%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

(5S)-5-(Hydroxymethyl)dihydro-2(3H)-furanone Structure

(5S)-5-(Hydroxy...

~%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose Structure

1-O-acetyl-5-O-...

~%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

(R)-5-(TERT-BUTYLDIPHENYLSILOXYMETHYL)DIHYDRO-2(3H)FURANONE Structure

(R)-5-(TERT-BUT...

~%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

N/A Structure

~%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone Structure

5-O-(tert-butyl...

~%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

6-chloro-9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl]-9H-purine Structure

6-chloro-9-[5-O...

~%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

N6-methyl-9-(5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl)adenine Structure

N6-methyl-9-(5-...

~%

[(2S,5R)-5-[6-(methylamino)purin-9-yl]-2,5-dihydrofuran-2-yl]methanol Structure

[(2S,5R)-5-[6-(...

N4-acetyl-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine Structure

N4-acetyl-1-(2,...

~91%

Zalcitabine Structure

6-chloro-9-(5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine Structure

6-chloro-9-(5-O...

~82%

(2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol Structure

(2S,5R)-5-(6-Ch...

(5S)-5-(Hydroxymethyl)dihydro-2(3H)-furanone Structure

(5S)-5-(Hydroxy...

~%

(2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol Structure

(2S,5R)-5-(6-Ch...

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose Structure

1-O-acetyl-5-O-...

~%

(2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol Structure

(2S,5R)-5-(6-Ch...

(R)-5-(TERT-BUTYLDIPHENYLSILOXYMETHYL)DIHYDRO-2(3H)FURANONE Structure

(R)-5-(TERT-BUT...

~%

(2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol Structure

(2S,5R)-5-(6-Ch...

N/A Structure

~%

(2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol Structure

(2S,5R)-5-(6-Ch...

5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone Structure

5-O-(tert-butyl...

~%

(2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol Structure

(2S,5R)-5-(6-Ch...

6-chloro-9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl]-9H-purine Structure

6-chloro-9-[5-O...

~%

(2S,5R)-5-(6-Chloro-9H-purine-9-yl)tetrahydro-2-furanmethanol Structure

(2S,5R)-5-(6-Ch...

1-(5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil Structure

1-(5-O-(tert-bu...

~82%

2',3'-Dideoxyuridine Structure

2',3'-Dideoxyuridine

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose Structure

1-O-acetyl-5-O-...

~%

2',3'-Dideoxyadenosine Structure

2',3'-Dideoxyad...

(R)-5-(TERT-BUTYLDIPHENYLSILOXYMETHYL)DIHYDRO-2(3H)FURANONE Structure

(R)-5-(TERT-BUT...

~%

2',3'-Dideoxyadenosine Structure

2',3'-Dideoxyad...

N/A Structure

~%

2',3'-Dideoxyadenosine Structure

2',3'-Dideoxyad...

5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone Structure

5-O-(tert-butyl...

~%

2',3'-Dideoxyadenosine Structure

2',3'-Dideoxyad...

6-chloro-9-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl]-9H-purine Structure

6-chloro-9-[5-O...

~%

2',3'-Dideoxyadenosine Structure

2',3'-Dideoxyad...

N/A Structure

~%

2',3'-Dideoxyadenosine Structure

2',3'-Dideoxyad...

1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl]thymine Structure

1-[5-O-(tert-bu...

~80%

2',3'-Dideoxythymidine Structure

2',3'-Dideoxyth...

(5S)-5-(Hydroxymethyl)dihydro-2(3H)-furanone Structure

(5S)-5-(Hydroxy...

~%

2',3'-Didehydro-2',3'-dideoxyuridine Structure

2',3'-Didehydro...

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose Structure

1-O-acetyl-5-O-...

~%

2',3'-Didehydro-2',3'-dideoxyuridine Structure

2',3'-Didehydro...

(R)-5-(TERT-BUTYLDIPHENYLSILOXYMETHYL)DIHYDRO-2(3H)FURANONE Structure

(R)-5-(TERT-BUT...

~%

2',3'-Didehydro-2',3'-dideoxyuridine Structure

2',3'-Didehydro...

N/A Structure

~%

2',3'-Didehydro-2',3'-dideoxyuridine Structure

2',3'-Didehydro...

5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone Structure

5-O-(tert-butyl...

~%

2',3'-Didehydro-2',3'-dideoxyuridine Structure

2',3'-Didehydro...

1-(5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl)uracil Structure

1-(5-O-(tert-bu...

~%

2',3'-Didehydro-2',3'-dideoxyuridine Structure

2',3'-Didehydro...

2-Amino-6-chloropurine Structure

2-Amino-6-chlor...

~86%

6-Chloro-2-fluoropurine Structure

6-Chloro-2-fluo...

Synthesis and structure-activity relationships of 6-substitu...

[Chu, Chung K.; Ullas, Giliyar V.; Jeong, Lak S.; Ahn, Soon K.; Doboszewski, Bogdan; et al. Journal of Medicinal Chemistry, 1990 , vol. 33, # 6 p. 1553 - 1561]

Synthesis and structure-activity relationships of 6-substitu...

[Chu, Chung K.; Ullas, Giliyar V.; Jeong, Lak S.; Ahn, Soon K.; Doboszewski, Bogdan; et al. Journal of Medicinal Chemistry, 1990 , vol. 33, # 6 p. 1553 - 1561]