2,2'-Anhydro-L-uridine

Base Information

• Chemical Name: 2,2'-Anhydro-L-uridine
• CAS No.: 31501-46-9
• Molecular Formula: C9H10 N2 O5
• Molecular Weight: 226.189
• DSSTox Substance ID: DTXSID30446477
• Wikidata: Q82265123
• Mol file: 31501-46-9.mol

Synonyms:2,2'-Anhydro-L-uridine;31501-46-9;(2S,4S,5S,6R)-5-hydroxy-4-(hydroxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one;SCHEMBL14208937;DTXSID30446477;(2S,4S,5S,6R)-5-hydroxy-4-(hydroxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.0,dodeca-8,11-dien-10-one

Chemical Property of 2,2'-Anhydro-L-uridine

Chemical Property:

• Boiling Point: 456.3±55.0 °C(Predicted)
• PKA: 12.55±0.40(Predicted)
• PSA: 93.81000
• Density: 2.01±0.1 g/cm3(Predicted)
• LogP: -1.74510
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 226.05897142
• Heavy Atom Count: 16
• Complexity: 393

Purity/Quality:

97% ^*data from raw suppliers

2,2''-Anhydro-L-uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN2C3C(C(C(O3)CO)O)OC2=NC1=O
• Isomeric SMILES: C1=CN2[C@@H]3[C@@H]([C@H]([C@@H](O3)CO)O)OC2=NC1=O

Technology Process of 2,2'-Anhydro-L-uridine

There total 15 articles about 2,2'-Anhydro-L-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: 86.0%

uridine (58-96-8) → (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one (31501-46-9)

Guidance literature:

uridine; With bis(phenyl) carbonate; In N,N-dimethyl-formamide; for 100h;

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 120 - 130 ℃; for 2h;

DOI:10.1080/15257770802581765

Reference yield: 74.0%

2-amino-β-L-arabinofurano[1',2':4,5]oxazoline (35939-60-7) + propynoic acid methyl ester (922-67-8) → (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one (31501-46-9)

Guidance literature:

In ethanol; water; for 2h; Reflux;

DOI:10.1021/jm301778x

Reference yield: 70.0%

L-uridine (58-96-8) → (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one (31501-46-9)

Guidance literature:

With bis(phenyl) carbonate; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1016/j.phytol.2020.01.018

upstream raw materials:

2-amino-β-L-arabinofurano[1',2':4,5]oxazoline

propynoic acid methyl ester

L-arabinose

CYANAMID

Downstream raw materials:

1-(β-L-arabinofuranosyl)-uracil

3',5'-di-O-benzoyl-2,2'-anhydro-L-uridine

1-<(β-L-arabinofuranosyl)-E-5-(2-bromovinyl)>uracil

Thiocarbonic acid O-[(2S,3S,4S,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-phenyl ester