1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine

Base Information

• Chemical Name: 1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine
• CAS No.: 239808-43-6
• Molecular Formula: C₃₇H₆₀N₄O₄Si₃
• Molecular Weight: 709.164

Synonyms:1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine

Chemical Property of 1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine

There total 14 articles about 1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine 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: 56.0%

1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]uracil (239808-42-5) → 1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine (239808-43-6)

Guidance literature:

1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]uracil; With dmap; 2,4,6-triisopropylphenylsulfonyl chloride; triethylamine; In acetonitrile; at 20 ℃; for 1.5h;

With ammonium hydroxide; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1248/cpb.47.1000

Reference yield:

meso-cis-1,4-diacetoxy-2-cyclopentene (60389-71-1,60410-14-2,61826-75-3) → 1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine (239808-43-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 34 percent / porcine liver esterase; phosphate buffer / 48 h / 37 °C / pH 7.0

2.1: imidazole / dimethylformamide / 24 h / 0 °C

3.1: 28 percent NaOMe / methanol / 24 h / 20 °C

4.1: 97 percent / pyridine / 1.5 h / 20 °C

5.1: 95 percent / Pd₂(dba)3*CHCl₃; PPh₃ / tetrahydrofuran / 3 h / 20 °C

6.1: 91 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: 93 percent / pyridine / 24 h / 20 °C

8.1: 84 percent / Pd₂(dba)3*CHCl₃; PPh₃; aq. NaOH / tetrahydrofuran / 7 h / 20 °C

9.1: 93 percent / NaOMe / methanol / 24 h / 20 °C

10.1: 86 percent / BCl₃ / CH₂Cl₂ / 24 h / 20 °C

11.1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

12.1: 67 percent / OsO₄; 4-methylmorpholine N-oxide; tert-BuOOH / 2-methyl-propan-2-ol / 4 h / 20 °C

13.1: 90 percent / imidazole / dimethylformamide / 48 h / 20 °C

14.1: 2,4,6-triisopropylbenzenesulfonyl chloride; Et₃N; dimethylaminopyridine / acetonitrile / 1.5 h / 20 °C

14.2: 56 percent / 28 percent aq. NH₄OH / acetonitrile / 3 h / 20 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; porcine liver esterase; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; osmium(VIII) oxide; 2,4,6-triisopropylphenylsulfonyl chloride; phosphate buffer; tetrabutyl ammonium fluoride; sodium methylate; boron trichloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: Substitution / 3.1: Deacetylation / 4.1: Substitution / 5.1: Substitution / 6.1: desilylation / 7.1: Substitution / 8.1: Substitution / 9.1: debenzoylation / 10.1: debenzylation / 11.1: Condensation / 12.1: dihydroxylation / 13.1: Condensation / 14.1: Substitution / 14.2: Substitution;

DOI:10.1248/cpb.47.1000

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → 1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine (239808-43-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: imidazole / dimethylformamide / 24 h / 0 °C

2.1: 28 percent NaOMe / methanol / 24 h / 20 °C

3.1: 97 percent / pyridine / 1.5 h / 20 °C

4.1: 95 percent / Pd₂(dba)3*CHCl₃; PPh₃ / tetrahydrofuran / 3 h / 20 °C

5.1: 91 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

6.1: 93 percent / pyridine / 24 h / 20 °C

7.1: 84 percent / Pd₂(dba)3*CHCl₃; PPh₃; aq. NaOH / tetrahydrofuran / 7 h / 20 °C

8.1: 93 percent / NaOMe / methanol / 24 h / 20 °C

9.1: 86 percent / BCl₃ / CH₂Cl₂ / 24 h / 20 °C

10.1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

11.1: 67 percent / OsO₄; 4-methylmorpholine N-oxide; tert-BuOOH / 2-methyl-propan-2-ol / 4 h / 20 °C

12.1: 90 percent / imidazole / dimethylformamide / 48 h / 20 °C

13.1: 2,4,6-triisopropylbenzenesulfonyl chloride; Et₃N; dimethylaminopyridine / acetonitrile / 1.5 h / 20 °C

13.2: 56 percent / 28 percent aq. NH₄OH / acetonitrile / 3 h / 20 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; osmium(VIII) oxide; 2,4,6-triisopropylphenylsulfonyl chloride; tetrabutyl ammonium fluoride; sodium methylate; boron trichloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Substitution / 2.1: Deacetylation / 3.1: Substitution / 4.1: Substitution / 5.1: desilylation / 6.1: Substitution / 7.1: Substitution / 8.1: debenzoylation / 9.1: debenzylation / 10.1: Condensation / 11.1: dihydroxylation / 12.1: Condensation / 13.1: Substitution / 13.2: Substitution;

DOI:10.1248/cpb.47.1000

upstream raw materials:

1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]uracil

meso-cis-1,4-diacetoxy-2-cyclopentene

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

1-[(1R,4S)-4-(N-hydroxyamino)-2-cyclopenten-1-yl]uracil

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