N⁶-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine

Base Information

• Chemical Name: N⁶-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine
• CAS No.: 812644-08-9
• Molecular Formula: C₂₁H₂₃N₅O₆
• Molecular Weight: 441.444
• Mol file: 812644-08-9.mol

Synonyms:N⁶-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine

Chemical Property of N⁶-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine

There total 2 articles about N⁶-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)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: 70.0%

2,2-dimethoxy-propane (77-76-9) + N-{9-[(2R,3R,4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide (898221-45-9) → N6-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine (812644-08-9)

Guidance literature:

2,2-dimethoxy-propane; N-{9-[(2R,3R,4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide; With 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; In acetone;

With acetic acid; In acetone;

DOI:10.1016/j.bmcl.2004.09.051

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-benzoylamino-purin-9-yl)-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester → N6-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine (812644-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 70 percent / aq. NaOH / ethanol

2.1: APTS / acetone

2.2: 70 percent / aq. AcOH / acetone

With sodium hydroxide; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; In ethanol; acetone;

DOI:10.1016/j.bmcl.2004.09.051

Reference yield: 60.0%

p-toluenesulfonyl chloride (98-59-9) + N6-benzoyl-2',3'-O-isopropylidene-9-(β-D-allofuranosyl)adenine (812644-08-9) → Toluene-4-sulfonic acid (R)-2-[(3aR,4R,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-hydroxy-ethyl ester (898221-48-2)

Guidance literature:

With pyridine;

DOI:10.1016/j.bmcl.2004.09.051

upstream raw materials:

2,2-dimethoxy-propane

N-{9-[(2R,3R,4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

Downstream raw materials:

Toluene-4-sulfonic acid (R)-2-[(3aR,4R,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-hydroxy-ethyl ester

N-[9-(2,2-dimethyl-6-thiiranyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-benzamide

N-[9-(2,2-dimethyl-6-oxiranyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-benzamide

N-[9-(2,2-dimethyl-6-oxiranyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-benzamide