1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-galacto-D-allo-undecofuranosyl-(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-galacto-D-allo-undecofuranosyl-(1,4)]uracil
• CAS No.: 719278-94-1
• Molecular Formula: C₃₆H₅₉N₅O₉SSi₂
• Molecular Weight: 794.13

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

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-galacto-D-allo-undecofuranosyl-(1,4)]uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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-galacto-D-allo-undecofuranosyl-(1,4)]uracil

There total 17 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-galacto-D-allo-undecofuranosyl-(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: 92.0%

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 (719278-93-0) → 1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-galacto-D-allo-undecofuranosyl-(1,4)]uracil (719278-94-1)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In dichloromethane;

DOI:10.1081/NCN-200059769

Reference yield:

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 (719278-95-2) → 1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-galacto-D-allo-undecofuranosyl-(1,4)]uracil (719278-94-1)

Guidance literature:

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; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -20 ℃; for 0.0833333h;

With sodium tetrahydroborate; acetic acid; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1081/NCN-120027831

Reference yield:

(3R,4R,5S)-5-azido-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)-2-hexanone (719278-92-9) → 1-[10-azido-2,3-di-O-(tert-butyldimethylsilyl)-6,10,11-trideoxy-8,9-O-isopropylidene-11-S-phenyl-11-thio-L-galacto-D-allo-undecofuranosyl-(1,4)]uracil (719278-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1: samarium diiodide / tetrahydrofuran

2: 92 percent / NaBH₄; acetic acid / CH₂Cl₂

With sodium tetrahydroborate; samarium diiodide; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1081/NCN-200059769

upstream raw materials:

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-phenylsulfinyl-L-galacto-D-allo-undecofuranosyl-(1,4)]uracil

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

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

Downstream raw materials:

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

acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

acetic acid 2-(7-amino-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

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

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