2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

Base Information

Chemical Name:2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine
CAS No.:300693-22-5
Molecular Formula:C₄₀H₄₅N₅O₁₃
Molecular Weight:803.823
Hs Code.:

Synonyms:2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

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Chemical Property of 2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

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Technology Process of 2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

There total 11 articles about 2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine 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: 82.0%

: 60855-35-8
6-benzoylamino-9-trimethylsilylpurine

: 1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2'-O-benzyl-α-D-glucopyranosyl)-5,6'-di-O-(butane-1,4-diyl)-D-ribofuranoside

: 300693-22-5
2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

Guidance literature:: With trifluoromethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 16h; Heating;
DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

: 100-39-0
benzyl bromide

: 300693-22-5
2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

Guidance literature:: Multi-step reaction with 8 steps

1: 4.40 g / NaH / dimethylformamide / 0 °C

2: 74 percent / TfOH / toluene; dioxane / 0.25 h

3: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

4: 89 percent / sodium hydride / dimethylformamide / 3 h / cooling

5: 75 percent / RuCl₂(PCy₃)2CHPh / toluene / 16 h

6: 0.21 g / H₂ / PtO₂ / ethyl acetate

7: 92 percent / H₂O; ethane-1,2-diol / 1.5 h / Heating

8: 82 percent / trifluoromethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 16 h / Heating

With trifluorormethanesulfonic acid; trifluoromethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Grubbs catalyst first generation; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; water; ethylene glycol; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Alkylation / 5: Cyclization / 6: Catalytic hydrogenation / 7: Acetylation / 8: Substitution;
DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

: 197644-79-4
(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

: 300693-22-5
2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / 2 h

2: 4.40 g / NaH / dimethylformamide / 0 °C

3: 74 percent / TfOH / toluene; dioxane / 0.25 h

4: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

5: 89 percent / sodium hydride / dimethylformamide / 3 h / cooling

6: 75 percent / RuCl₂(PCy₃)2CHPh / toluene / 16 h

7: 0.21 g / H₂ / PtO₂ / ethyl acetate

8: 92 percent / H₂O; ethane-1,2-diol / 1.5 h / Heating

9: 82 percent / trifluoromethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 16 h / Heating

With pyridine; trifluorormethanesulfonic acid; trifluoromethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Grubbs catalyst first generation; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; water; ethylene glycol; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Substitution / 4: Hydrolysis / 5: Alkylation / 6: Cyclization / 7: Catalytic hydrogenation / 8: Acetylation / 9: Substitution;
DOI:10.1016/S0040-4020(00)00480-4