1-C-[2,4-Bis(1,1-diMethylethoxy)-5-pyriMidinyl]-5-O-(1-Methoxy-1-Methylethyl)-2,3-O-(1-Methylethylidene)-α-D-ribofuranose

Base Information

• Chemical Name: 1-C-[2,4-Bis(1,1-diMethylethoxy)-5-pyriMidinyl]-5-O-(1-Methoxy-1-Methylethyl)-2,3-O-(1-Methylethylidene)-α-D-ribofuranose
• CAS No.: 631920-67-7
• Molecular Formula: C₂₄H₄₀N₂O₈
• Molecular Weight: 484.59
• Mol file: 631920-67-7.mol

Synonyms:

Chemical Property of 1-C-[2,4-Bis(1,1-diMethylethoxy)-5-pyriMidinyl]-5-O-(1-Methoxy-1-Methylethyl)-2,3-O-(1-Methylethylidene)-α-D-ribofuranose

Chemical Property:

• Boiling Point: 585.7±60.0 °C(Predicted)
• PKA: 9.42±0.60(Predicted)
• Density: 1.133±0.06 g/cm3(Predicted)
• Solubility.: DCM, Ethyl Acetate, Methanol

Purity/Quality:

95% ^*data from raw suppliers

1-C-[2,4-Bis(1,1-dimethylethoxy)-5-pyrimidinyl]-5-O-(1-methoxy-1-methylethyl)-2,3-O-(1-methylethylidene)-α-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-C-[2,4-Bis(1,1-dimethylethoxy)-5-pyrimidinyl]-5-O-(1-methoxy-1-methylethyl)-2,3-O-(1-methylethylidene)-α-D-ribofuranose is an intermediate in the synthesis of β-Pseudouridine (O839607), an isomer of the nucleoside uridine found in all species and in many classes of RNA except mRNA.

Technology Process of 1-C-[2,4-Bis(1,1-diMethylethoxy)-5-pyriMidinyl]-5-O-(1-Methoxy-1-Methylethyl)-2,3-O-(1-Methylethylidene)-α-D-ribofuranose

There total 2 articles about 1-C-[2,4-Bis(1,1-diMethylethoxy)-5-pyriMidinyl]-5-O-(1-Methoxy-1-Methylethyl)-2,3-O-(1-Methylethylidene)-α-D-ribofuranose 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: 89.0%

2,3-O-isopropylidene-5-O-(1-methoxy-1-methyl-ethyl)-D-ribono-1,4-lactone (162635-53-2) + 5-lithio-2,4-di-t-butoxypyrimidine (62880-74-4) → 4-(2,4-di-tert-butoxy-pyrimidin-5-yl)-6-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol (631920-67-7)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2003.09.103

Reference yield:

D-Ribono-1,4-lactone (5336-08-3) → 4-(2,4-di-tert-butoxy-pyrimidin-5-yl)-6-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol (631920-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridinium p-toluenesulfonate; sodium sulfate / 1 h / 60 °C

2: 89 percent / tetrahydrofuran / -78 °C

With pyridinium p-toluenesulfonate; sodium sulfate; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2003.09.103

upstream raw materials:

2,3-O-isopropylidene-5-O-(1-methoxy-1-methyl-ethyl)-D-ribono-1,4-lactone

5-lithio-2,4-di-t-butoxypyrimidine

D-Ribono-1,4-lactone