(2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran

Base Information

• Chemical Name: (2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran
• CAS No.: 630104-51-7
• Molecular Formula: C₂₃H₂₈N₂O₆
• Molecular Weight: 428.485

Synonyms:(2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran

Chemical Property of (2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran

There total 11 articles about (2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran 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: 93.0%

allyl bromide (106-95-6) + (2S,3S,4R,5R)-5-(2',4'-dimethoxypyrimidin-5'-yl)-4-(4'-methoxybenzyloxy)-2-vinyltetrahydrofuran-3-ol (630104-50-6) → (2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran (630104-51-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/ol030095k

Reference yield:

(2S,3S,4R,5R)-2-(2,4-dimethoxypyrimidin-5-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol (68168-19-4) → (2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran (630104-51-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / pyridine

2.1: 84 percent / NaH / tetrahydrofuran; dimethylformamide

3.1: 88 percent / hydrochloric acid / dioxane

4.1: DMSO; (COCl)2; diisopropylethylamine / CH₂Cl₂

4.2: 36 percent / NaHMDS / tetrahydrofuran

5.1: 93 percent / NaH / dimethylformamide / 2 h / 20 °C

With pyridine; hydrogenchloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol030095k

Reference yield:

2,3-O-isopropylidene-5-O-(1-methoxy-1-methyl-ethyl)-D-ribono-1,4-lactone (162635-53-2) → (2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran (630104-51-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 75 percent / t-BuLi

2.1: 86 percent / L-Selectride; ZnCl₂ / CH₂Cl₂

3.1: 91 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran

4.1: 85 percent / acetic acid

5.1: 89 percent / pyridine

6.1: 84 percent / NaH / tetrahydrofuran; dimethylformamide

7.1: 88 percent / hydrochloric acid / dioxane

8.1: DMSO; (COCl)2; diisopropylethylamine / CH₂Cl₂

8.2: 36 percent / NaHMDS / tetrahydrofuran

9.1: 93 percent / NaH / dimethylformamide / 2 h / 20 °C

With pyridine; hydrogenchloride; oxalyl dichloride; di-isopropyl azodicarboxylate; tert.-butyl lithium; L-Selectride; sodium hydride; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 3.1: Mitsunobu reaction;

DOI:10.1021/ol030095k

upstream raw materials:

allyl bromide

(2S,3S,4R,5R)-5-(2',4'-dimethoxypyrimidin-5'-yl)-4-(4'-methoxybenzyloxy)-2-vinyltetrahydrofuran-3-ol

C₃₂H₅₂N₂O₈Si₂

(2S,3S,4R,5R)-2-(2,4-dimethoxypyrimidin-5-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol

Downstream raw materials:

5-[(2S,3S,3aR,6S,7R,7aR)-7-Azido-6-ethoxy-3-(4-methoxy-benzyloxy)-hexahydro-furo[3,2-b]pyran-2-yl]-2,4-dimethoxy-pyrimidine

(2S,3S,3aR,6R,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-hydroxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

(2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

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