1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

Base Information

Chemical Name:1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil
CAS No.:719278-93-0
Molecular Formula:C₃₆H₅₇N₅O₉SSi₂
Molecular Weight:792.114
Hs Code.:

1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

Synonyms:1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

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Chemical Property of 1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

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Technology Process of 1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

There total 16 articles about 1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 47.0%

: 719278-92-9
(3R,4R,5S)-5-azido-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)-2-hexanone

: 161867-43-2
(2S,3R,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carbaldehyde

: 719278-93-0
1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

: 1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-talo-undeculofuranosyl-(1,4)]uracil

Guidance literature:: (3R,4R,5S)-5-azido-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)-2-hexanone; With samarium diiodide; oxygen; In tetrahydrofuran; at -40 ℃;

(2S,3R,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carbaldehyde; In tetrahydrofuran; at -78 ℃; for 0.25h;
DOI:10.1081/NCN-120027831

Reference yield:

: 719278-95-2
1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-phenylsulfinyl-L-galacto-D-allo-undecofuranosyl-(1,4)]uracil

: 719278-93-0
1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

: 719278-96-3
1-[(2R,3R,4R,5R)-5-[(R)-2-((3aS,4R,6S,7R,7aR)-7-Azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-hydroxy-ethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -20 ℃; for 0.0833333h; Title compound not separated from byproducts;
DOI:10.1081/NCN-120027831

Reference yield:

: (3aR,4S,6R,7R,7aR)-7-Azido-2,2-dimethyl-4-phenylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol

: 719278-93-0
1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-lyxo-D-allo-undeculofuranosyl-(1,4)]uracil

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1.83 g / sodium borohydride / methanol / 0.5 h / -20 °C

2.1: imidazole / dimethylformamide / 1 h / 0 °C

3.1: pyridine / 12 h / 20 °C

4.1: 534 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

5.1: pyridine / CH₂Cl₂ / 0.08 h / -20 °C

6.1: 614 mg / Et₃N / CH₂Cl₂ / 1 h / 20 °C

7.1: 90 percent / NaOMe / methanol / 1 h / 20 °C

8.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

9.1: samarium diiodide; O₂ / tetrahydrofuran / -40 °C

9.2: tetrahydrofuran / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; samarium diiodide; tetrabutyl ammonium fluoride; oxygen; sodium methylate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1081/NCN-120027831