4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 206055-83-6
• Molecular Formula: C₂₅H₃₀O₇
• Molecular Weight: 442.509
• Mol file: 206055-83-6.mol

Synonyms:4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property of 4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

There total 1 articles about 4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 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-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (206055-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, -5 deg C, 1.5 h, 2.) room temperature, 3 h

2: 90 percent / pyridine / 3 h / Ambient temperature

With sodium hydride; In pyridine;

DOI:10.1016/S0040-4020(98)00094-5

Reference yield:

4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (206055-83-6) → 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione (206055-71-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 80percent AcOH / 4 h / 90 °C

2: pyridine / 72 h / Ambient temperature

3: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

4: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature

5: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h

6: 98 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

7: 93 percent / pyridine / 2 h / Ambient temperature

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; acetic acid; p-toluenesulfonyl chloride; palladium dihydroxide; In pyridine; methanol; ethanol;

DOI:10.1016/S0040-4020(98)00094-5

Reference yield:

4-C-acetoxymethyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (206055-83-6) → (1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane (206055-75-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 80percent AcOH / 4 h / 90 °C

2: pyridine / 72 h / Ambient temperature

3: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

4: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature

5: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h

6: 98 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

7: 93 percent / pyridine / 2 h / Ambient temperature

8: 70 percent / iPr₂EtN / CH₂Cl₂ / 1 h

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; palladium dihydroxide; In pyridine; methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(98)00094-5

upstream raw materials:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Downstream raw materials:

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

1-[(2R,3R,4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-3-hydroxy-5-(hydroxymethyl)tetra-hydrofuran-2-yl]-5-methylpyrimidine-2,4-dione

[(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate