N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine
• CAS No.: 124572-55-0
• Molecular Formula: C₃₄H₂₉N₅O₈
• Molecular Weight: 635.633
• Mol file: 124572-55-0.mol

Synonyms:

Chemical Property of N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine

There total 22 articles about N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine 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:

1,2-O-Isopropyliden-6-O-triphenylmethyl-5-desoxy-α-D-xylo-hexofuran-5-enose (4056-10-4) → N6-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine (124572-55-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / triethylamine / dioxane / 1 h / Ambient temperature

2: acetic acid / dioxane; H₂O / 0.75 h / Heating

3: sodium borohydride / ethanol / 0.25 h / Ambient temperature

4: 95 percent / pyridine / 24 h / 20 °C

5: 97 percent / sodium methylate / methanol / 0.5 h / Ambient temperature

6: 1)dimethyl sulfoxide/acetic anhydride, 2)sodium borohydride / 1)1.5h, 70 deg C, 2)1h, room temperature

7: 85 percent / triethylamine / dioxane / 1 h / 20 °C

8: 89 percent / tin tetrachloride / 1,2-dichloro-ethane / 0.08 h / 20 °C

9: 86 percent / triethylamine / dioxane / 1 h / 20 °C

10: 80 percent / sulfuric acid / acetic acid / 18 h / 20 °C

11: 1)1,1,1,3,3,3-hexamethyldisilazane 2)trimethylsilyl trifluormethanesulfonate / 1) pyridine, 2) 1,2-dichloroethane, 1.5 h, reflux

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; acetic anhydride; tin(IV) chloride; acetic acid; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; pyridine; methanol; ethanol; water; acetic acid; 1,2-dichloro-ethane;

Reference yield:

1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose (7057-09-2) → N6-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine (124572-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / pyridine / 24 h / 20 °C

2: 1)dimethyl sulfoxide/acetic anhydride, 2)sodium borohydride / 1)1.5h, 70 deg C, 2)1h, room temperature

3: 85 percent / triethylamine / dioxane / 1 h / 20 °C

4: 89 percent / tin tetrachloride / 1,2-dichloro-ethane / 0.08 h / 20 °C

5: 86 percent / triethylamine / dioxane / 1 h / 20 °C

6: 80 percent / sulfuric acid / acetic acid / 18 h / 20 °C

7: 1)1,1,1,3,3,3-hexamethyldisilazane 2)trimethylsilyl trifluormethanesulfonate / 1) pyridine, 2) 1,2-dichloroethane, 1.5 h, reflux

With pyridine; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic anhydride; tin(IV) chloride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; acetic acid; 1,2-dichloro-ethane;

Reference yield:

Benzoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-oxo-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester → N6-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine (124572-55-0)

Guidance literature:

Multi-step reaction with 9 steps

1: sodium borohydride / ethanol / 0.25 h / Ambient temperature

2: 95 percent / pyridine / 24 h / 20 °C

3: 97 percent / sodium methylate / methanol / 0.5 h / Ambient temperature

4: 1)dimethyl sulfoxide/acetic anhydride, 2)sodium borohydride / 1)1.5h, 70 deg C, 2)1h, room temperature

5: 85 percent / triethylamine / dioxane / 1 h / 20 °C

6: 89 percent / tin tetrachloride / 1,2-dichloro-ethane / 0.08 h / 20 °C

7: 86 percent / triethylamine / dioxane / 1 h / 20 °C

8: 80 percent / sulfuric acid / acetic acid / 18 h / 20 °C

9: 1)1,1,1,3,3,3-hexamethyldisilazane 2)trimethylsilyl trifluormethanesulfonate / 1) pyridine, 2) 1,2-dichloroethane, 1.5 h, reflux

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; acetic anhydride; tin(IV) chloride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; pyridine; methanol; ethanol; acetic acid; 1,2-dichloro-ethane;

upstream raw materials:

acetic anhydride

3,6-di-O-benzoyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-hexofuranose

6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose

Downstream raw materials:

9-(5-Desoxy-β-D-ribo-hexofuranosyl)adenin