(1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine

Base Information

• Chemical Name: (1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine
• CAS No.: 660410-88-8
• Molecular Formula: C₄₃H₄₅N₃O₇Si
• Molecular Weight: 743.932

Synonyms:(1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine

Chemical Property of (1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine

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Technology Process of (1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine

There total 4 articles about (1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine 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: 53.0%

N-(5-methyl-2-oxo-1H-pyrimidin-4-yl)benzamide (126354-30-1) + (1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane (389633-40-3) → (1'S,3'R,4'R,5'R,7'R)-N4-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine (660410-87-7) + (1'S,3'R,4'R,5'R,7'S)-N4-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine (660410-88-8)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; In acetonitrile; at 50 ℃; for 4h;

DOI:10.1021/ja037211z

Reference yield:

(3aS,5R,6R,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3a-phenyl-hexahydro-furo[3,2-b]furan-2,6-diol → (1'S,3'R,4'R,5'R,7'S)-N4-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine (660410-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 39 h / 20 °C

2: 53 percent / N,O-bis(trimethylsilyl)acetamide; SnCl₄ / acetonitrile / 4 h / 50 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; In acetonitrile;

DOI:10.1021/ja037211z

Reference yield:

[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetaldehyde → (1'S,3'R,4'R,5'R,7'S)-N4-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-5-methylcytosine (660410-88-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 269 mg / aq. H₂SO₄ / tetrahydrofuran / 6 h / 60 °C

2: 90 percent / pyridine / 39 h / 20 °C

3: 53 percent / N,O-bis(trimethylsilyl)acetamide; SnCl₄ / acetonitrile / 4 h / 50 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; tin(IV) chloride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja037211z

upstream raw materials:

N-(5-methyl-2-oxo-1H-pyrimidin-4-yl)benzamide

(1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane

Downstream raw materials:

(1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-(4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl)-5-methylcytosine

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