(6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone

Base Information

• Chemical Name: (6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone
• CAS No.: 335593-87-8
• Molecular Formula: C₃₂H₃₀N₄O₉
• Molecular Weight: 614.612
• Mol file: 335593-87-8.mol

Synonyms:(6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone

Chemical Property of (6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone

There total 1 articles about (6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone 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: 96.0%

aminoguanidine bicarbonate (2582-30-1) + 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3<2H,6H>-one (121701-32-4) → (6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone (335593-87-8)

Guidance literature:

In acetic acid; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(01)00017-9

Reference yield: 51.0%

(6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone (335593-87-8) → 2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine (335593-88-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 60 ℃; for 0.666667h;

DOI:10.1016/S0008-6215(01)00017-9

Reference yield:

(6S)- and (6R)-6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3-(2H,6H)iminosemicarbazone (335593-87-8) → 2-amino-5-cyano-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine (335593-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 51 percent / cc. HCl / dioxane / 0.67 h / 60 °C

2: 69 percent / POCl₃ / 0.67 h / 80 °C

3: 59 percent / hydroxylamine hydrochloride / methanol / 3 h / Heating

4: 44 percent / trietylamine; trfluoromethanesulfonic anhydride / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; trifluoromethylsulfonic anhydride; hydroxylamine hydrochloride; triethylamine; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1016/S0008-6215(01)00017-9

upstream raw materials:

aminoguanidine bicarbonate

6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3<2H,6H>-one

Downstream raw materials:

2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine

2-amino-5-cyano-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine

2-(N,N-dimethylaminomethyleneamino)-5-formyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine

(E)-2-amino-5-hydroxyiminomethyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine