2',3'-Isopropylidene-isocytidine

Base Information

• Chemical Name: 2',3'-Isopropylidene-isocytidine
• CAS No.: 5975-05-3
• Molecular Formula: C12H17N3O5
• Molecular Weight: 283.28
• Mol file: 5975-05-3.mol

Synonyms:2',3'-Isopropylidene-isocytidine;2',3'-Di-O-isopropylidene-isocytidine;2-Amino-1-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-4(1H)-pyrimidinone;2',3'-O-Isopropylideneisocytidine

Chemical Property of 2',3'-Isopropylidene-isocytidine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidin-4(1H)-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',3'-Isopropylidene-isocytidine

There total 6 articles about 2',3'-Isopropylidene-isocytidine 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: 50.0%

2,2-dimethoxy-propane (77-76-9) + 2-amino-1-(β-D-ribofuranosyl)pyrimidin-4(1H)-one (489-59-8) → 2',3'-O-Isopropyliden-isocytidin (5975-05-3)

Guidance literature:

With toluene-4-sulfonic acid; for 2h; Ambient temperature;

DOI:10.1246/bcsj.53.3670

Reference yield:

uridine (58-96-8) → 2',3'-O-Isopropyliden-isocytidin (5975-05-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

2: sat. NH₃/MeOH / 120 h / Ambient temperature

3: 50 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

With methanol; ammonia; toluene-4-sulfonic acid; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1246/bcsj.53.3670

Reference yield:

(3aR,4R,12R,12aR)-2,2,2-triphenyl-4,5,12,12a-tetrahydro-2H,3aH,8H-4,12-epoxy-2λ5-[1,3,2]dioxaphospholo[4,5-e]pyrimido[2,1-b][1,3]-oxazocin-8-one (53337-87-4) → 2',3'-O-Isopropyliden-isocytidin (5975-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sat. NH₃/MeOH / 120 h / Ambient temperature

2: 50 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

With methanol; ammonia; toluene-4-sulfonic acid;

DOI:10.1246/bcsj.53.3670

upstream raw materials:

2',3'-O-isopropylidene-O²,5'-cyclouridine

2,2-dimethoxy-propane

2-amino-1-(β-D-ribofuranosyl)pyrimidin-4(1H)-one

(3aR,4R,12R,12aR)-2,2,2-triphenyl-4,5,12,12a-tetrahydro-2H,3aH,8H-4,12-epoxy-2λ5-[1,3,2]dioxaphospholo[4,5-e]pyrimido[2,1-b][1,3]-oxazocin-8-one

Refernces

• 1、 Kimura, Junji,Yagi, Kentaro,Suzuki, Hideyuki,Mitsunobu, Oyo. "Studies on Nucleosides and Nucleotides. VIII. Preparation and Reactions of Triphenylphosphoranediylnucleosides". . p. 3670 - 3677. Retrieved 2007/10/02.