3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione
• CAS No.: 191479-26-2
• Molecular Formula: C₂₀H₂₄N₂O₇
• Molecular Weight: 404.42
• Mol file: 191479-26-2.mol

Synonyms:3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

Chemical Property of 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

There total 6 articles about 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione 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: 96.0%

Benzyloxymethyl chloride (3587-60-8) + 2',3'-O-isopropylideneuridine (362-43-6) → 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione (191479-26-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 ℃; for 0.666667h;

DOI:10.1021/acs.orglett.7b03623

Reference yield: 94.0%

3-Benzyloxymethyl-1-[(3aR,4R,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-pyrimidine-2,4-dione (191479-25-1) → 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione (191479-26-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h;

DOI:10.1016/S0968-0896(97)00005-9

Reference yield:

uridine (58-96-8) → 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione (191479-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 22 h / 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.67 h / 0 °C

With sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.7b03623

upstream raw materials:

3-Benzyloxymethyl-1-[(3aR,4R,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1H-pyrimidine-2,4-dione

Benzyloxymethyl chloride

5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine

2',3'-O-isopropylideneuridine

Downstream raw materials:

Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

2',3'-O-isopropylideneuridine

2',3'-O-isopropylidene-5,6-dihydrouridine