2-[2,3-O-(1-Methylethylidene)-beta-D-ribofuranosyl]-4-thiazolecarboxamide

Base Information

• Chemical Name: 2-[2,3-O-(1-Methylethylidene)-beta-D-ribofuranosyl]-4-thiazolecarboxamide
• CAS No.: 60084-11-9
• Molecular Formula: C₁₂H₁₆N₂O₅S
• Molecular Weight: 300.335
• DSSTox Substance ID: DTXSID301155067
• Mol file: 60084-11-9.mol

Synonyms:60084-11-9;2-[2,3-O-(1-Methylethylidene)-beta-D-ribofuranosyl]-4-thiazolecarboxamide;SCHEMBL10740595;DTXSID301155067;2-((3AR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)thiazole-4-carboxamide

Chemical Property of 2-[2,3-O-(1-Methylethylidene)-beta-D-ribofuranosyl]-4-thiazolecarboxamide

Chemical Property:

• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 300.07799279
• Heavy Atom Count: 20
• Complexity: 407

Purity/Quality:

95% ^*data from raw suppliers

2-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-4-thiazolecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)C3=NC(=CS3)C(=O)N)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)C3=NC(=CS3)C(=O)N)CO)C
• Uses: 2-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-4-thiazolecarboxamide is an intermediate in the synthesis of Tiazofurin (T437200), an potential therapeutic agent in the treatment of cancer.

Technology Process of 2-[2,3-O-(1-Methylethylidene)-beta-D-ribofuranosyl]-4-thiazolecarboxamide

There total 4 articles about 2-[2,3-O-(1-Methylethylidene)-beta-D-ribofuranosyl]-4-thiazolecarboxamide 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: 73.0%

tiazofurin (60084-10-8) + acetone (67-64-1) → 2-(2',3'-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxamide (60084-11-9)

Guidance literature:

With hydrogenchloride; In various solvent(s); Ambient temperature;

DOI:10.1021/jm00360a025

Reference yield: 51.0%

tiazofurin (60084-10-8) + 2,2-dimethoxy-propane (77-76-9) → 2-(2',3'-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxamide (60084-11-9)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; for 1h; Heating;

DOI:10.1016/j.ejmech.2006.01.005

Reference yield:

2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonthioamide (57944-10-2) → 2-(2',3'-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxamide (60084-11-9)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol

2: NH₃ / methanol

3: HC(OEt)3, HCl

With hydrogenchloride; ammonia; orthoformic acid triethyl ester; In methanol; ethanol;

DOI:10.1021/jo00888a005

upstream raw materials:

tiazofurin

acetone

2,2-dimethoxy-propane

2,5-anhydro-3,4,6-tri-O-benzoyl-D-allonthioamide

Downstream raw materials:

adenosine 5'- 5'<*>5'-ester with 2-β-D-ribofuranosyl-4-thiazolecarboxamide

2',3'-O-isopropylidene-5'-O-tosyltiazofurin

{Benzyloxy-[(3aR,4R,6R,6aR)-6-(4-carbamoyl-thiazol-2-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-phosphorylmethyl}-phosphonic acid dibenzyl ester

2-(5-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)thiazole-4-carboxamide