3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose
• CAS No.: 110808-85-0
• Molecular Formula: C₂₅H₃₀O₇
• Molecular Weight: 442.509
• Mol file: 110808-85-0.mol

Synonyms:

Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose

There total 1 articles about 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose 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:

3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose (55533-86-3,120615-67-0) + 4-methyl-benzoyl chloride (874-60-2) → 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose (110808-85-0)

Guidance literature:

With dibutylstannoxane; triethylamine; Yield given. Multistep reaction; 1.) methanol, reflux, 1 h; 2.) methanol, 20 deg C, 2 h;

DOI:10.1016/0008-6215(87)80059-9

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose (110808-85-0) → 2'-methyl-adenosine (15397-12-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) CF₃COOH; 2.) NaIO₄; 3.) MeONa

2: 82 percent / 20 percent Pd(OH)2/C / ethanol; cyclohexene / 2.5 h / Heating

3: 90 percent / 4-dimethylaminopyridine / pyridine / 16 h / 20 °C

4: 1.) hexamethyldisilazane; 2.) CF₃SO₂SiMe₃ / 1.) pyridine, reflux, 4 h; 2.) 1,2-dichloroethane, roomtemp., 7 d

5: 76 percent / ammonia / methanol / 48 h / 20 °C

With dmap; sodium periodate; ammonia; sodium methylate; trimethyl((trifluoromethyl)sulfonyl)silane; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; palladium dihydroxide; In pyridine; methanol; ethanol; cyclohexene;

DOI:10.1016/0008-6215(87)80059-9

Reference yield:

acetic anhydride (108-24-7) + 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-6-O-methylbenzoyl-α-D-allofuranose (110808-85-0) → 1,3-di-O-acetyl-2-O-benzyl-2-C-methyl-5-O-p-methylbenzoyl-β-D-ribofuranose (114952-95-3)

Guidance literature:

With sodium periodate; sodium methylate; trifluoroacetic acid; Yield given. Multistep reaction;

DOI:10.1016/0008-6215(87)80059-9

upstream raw materials:

3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose

4-methyl-benzoyl chloride

Downstream raw materials:

1,3-di-O-acetyl-2-O-benzyl-2-C-methyl-5-O-p-methylbenzoyl-β-D-ribofuranose

2'-methyl-adenosine

Refernces