2',3'-O-Isopropylidene-5-hydroxyMethyl uridine

Base Information

• Chemical Name: 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine
• CAS No.: 3816-77-1
• Molecular Formula: C13H18N2O7
• Molecular Weight: 314.29100
• Mol file: 3816-77-1.mol

Synonyms:1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5-hydroxy-methyluracil;5-hydroxymethyl-2',3'-O-isopropylideneuridine;5-hydroxymethyl-O2',O3'-isopropylidene-uridine;5-hydroxymethyl-2',3'-isopropylidene-uridine;2',3'-O-isopropylidene-5-hydroxymethyluridine;

Chemical Property of 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine

Chemical Property:

• PSA: 123.01000
• LogP: -1.56130

Purity/Quality:

97% ^*data from raw suppliers

5-(Hydroxymethyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 2',3'-O-Isopropylidene-5-hydroxymethyl uridine is a chemically modified nucleoside derivative where the 2' and 3' hydroxyl groups of the ribose moiety are protected by an isopropylidene group, and the 5-position of the uracil base is substituted with a hydroxymethyl group. This modification enhances the stability of the ribose ring and introduces a reactive hydroxymethyl functionality, making it a valuable intermediate in nucleoside chemistry for further derivatization or prodrug development. 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine is commonly used in synthetic applications, particularly in the preparation of modified nucleotides or as a precursor for antiviral or anticancer agents.

Technology Process of 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine

There total 5 articles about 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine 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: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2',3'-O-isopropylideneuridine (362-43-6) → 2',3'-O-isopropylidene-5-hydroxymethyl-uridine (3816-77-1)

Guidance literature:

With potassium hydroxide; for 0.05h; microwave irradiation;

DOI:10.1055/s-2002-35592

Reference yield:

uridine (58-96-8) → 2',3'-O-isopropylidene-5-hydroxymethyl-uridine (3816-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / p-toluenesulfonic acid monohydrate / acetone

2: 31 percent / KOH / H₂O / 48 h / 60 °C

With potassium hydroxide; toluene-4-sulfonic acid; In water; acetone;

DOI:10.1016/j.tetlet.2006.09.083

Reference yield:

2,3-O-isopropylidene-5-ethoxycarbonylpropylaminomethyluridine (60170-16-3) → 2',3'-O-isopropylidene-5-hydroxymethyl-uridine (3816-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) ZnCl₂, 2.) NaCNBH₃ / 1.) MeOH, RT, 20 min, 2.) MeOH, RT, 36 h

2: 9 percent / 2.67 h / 195 - 200 °C / 5 Torr

3: 80 percent / aq. KOH / 50 °C

With potassium hydroxide; sodium cyanoborohydride; zinc(II) chloride;

DOI:10.1006/bioo.1994.1034

upstream raw materials:

formaldehyd

2',3'-O-isopropylideneuridine

uridine

2,3-O-isopropylidene-5-ethoxycarbonylpropylaminomethyluridine

Downstream raw materials:

2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine

C₅₁H₅₄N₅O₁₇PS

5-carboxymethylaminomethyluridine

5-methylaminomethyluridine