Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Base Information

• Chemical Name: Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester
• CAS No.: 199458-04-3
• Molecular Formula: C₂₈H₃₆N₂O₇SSi
• Molecular Weight: 572.755
• Mol file: 199458-04-3.mol

Synonyms:

Chemical Property of Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

There total 1 articles about Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester 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:

methylmagnesium bromide (75-16-1) + methanesulfonyl chloride (124-63-0) + 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester (199458-04-3)

Guidance literature:

Yield given. Multistep reaction; 1.) THF, ether, -78 deg C to rt, 3 h; 2.) pyridine, 0 deg C, 1 h;

DOI:10.1055/s-1997-1003

Reference yield:

Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester (199458-04-3) → 4-Bromo-N-{(R)-1-[(2R,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-benzamide

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaN₃; 2.) SnCl₂*H₂O / 1.) DMF, 65 deg C, 5 h; 2.) MeOH, rt, 16 h

2: O-(1H benzotriazol-1-yl)-N,N,N',N'-tetramethyl uronium tetrafluoroborate, hydroxybenzotriazole, Et₃N / acetonitrile; tetrahydrofuran / rt, 1 h; 0 deg C to rt, 15 h

With sodium azide; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; tin(ll) chloride; In tetrahydrofuran; acetonitrile;

DOI:10.1055/s-1997-1003

Reference yield:

Methanesulfonic acid 1-[(2S,3S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester (199458-04-3) → C55H67N5O9Si2 (199458-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaN₃; 2.) SnCl₂*H₂O / 1.) DMF, 65 deg C, 5 h; 2.) MeOH, rt, 16 h

2: 94 percent / O-(1H benzotriazol-1-yl)-N,N,N',N'-tetramethyl uronium tetrafluoroborate, hydroxybenzotriazole, Et₃N / acetonitrile / 0 deg C, 1 h; 0 deg C to rt, 14 h

With sodium azide; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; tin(ll) chloride; In acetonitrile;

DOI:10.1055/s-1997-1003

upstream raw materials:

methylmagnesium bromide

methanesulfonyl chloride

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil

Downstream raw materials:

1-[(2R,4S,5R)-5-((S)-1-Amino-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

1-[(2R,4S,5R)-5-((R)-1-Amino-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

C₅₅H₆₇N₅O₉Si₂

C₅₅H₆₇N₅O₉Si₂