10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione

Base Information

• Chemical Name: 10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione
• CAS No.: 136738-78-8
• Molecular Formula: C₃₈H₄₀N₄O₁₂
• Molecular Weight: 744.755
• Mol file: 136738-78-8.mol

Synonyms:10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione

Chemical Property of 10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione

There total 26 articles about 10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione 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: 85.5%

10-[(4S,5S,6R)-6-[(3aR,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-5-hydroxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione (136738-77-7,136781-02-7) → 10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione (136738-78-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In dichloromethane; N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86553-4

Reference yield:

2-Chloroethyl β-D-ribofuranoside (64526-71-2,64949-99-1,64950-04-5) → 10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4S,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione (136738-78-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 93.2 percent / imidazole / dimethylformamide / 0.5 h / Ambient temperature

2: 90.8 percent / PPTS / CH₂Cl₂ / 1 h / Ambient temperature

3: 65 percent / sodium benzenesulfinate, KI / dimethylformamide / 6 h / 100 °C

4: 65 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

5: 35.5 mg / BF₃-Et₂O / CH₂Cl₂ / 0 °C

6: 85.5 percent / n-Bu₄NF / CH₂Cl₂; dimethylformamide / 0.5 h / Ambient temperature

With 1H-imidazole; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium benzenesulfonate; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86553-4

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 10-[(4S,5S,6R)-5-Hydroxy-6-[(3aR,4R,6R,6aR)-6-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione (136738-78-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 122 g / p-toluenesulfonic acid (pTsOH) / 12 h / Ambient temperature

2: 3.4percent KOH-MeOH / methanol / 3 h / Ambient temperature

3: 93.2 percent / imidazole / dimethylformamide / 0.5 h / Ambient temperature

4: 90.8 percent / PPTS / CH₂Cl₂ / 1 h / Ambient temperature

5: 65 percent / sodium benzenesulfinate, KI / dimethylformamide / 6 h / 100 °C

6: 65 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

7: 10.0 mg / BF₃-Et₂O / CH₂Cl₂ / 0 °C

8: n-Bu₄NF / CH₂Cl₂; dimethylformamide / Ambient temperature

With 1H-imidazole; potassium hydroxide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium benzenesulfonate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86553-4

upstream raw materials:

10-[(4S,5S,6R)-6-[(3aR,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxymethyl]-5-hydroxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

5'-O-Trityl riboflavin

2-Chloroethyl β-D-ribofuranoside