9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine

Base Information

• Chemical Name: 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine
• CAS No.: 151359-36-3
• Molecular Formula: C₁₃H₁₉N₅O₄
• Molecular Weight: 309.325
• Mol file: 151359-36-3.mol

Synonyms:9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine

Chemical Property of 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine

There total 4 articles about 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]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: 28.0%

2',3'-isopropylideneadenosine-1-oxide (5167-12-4) → 2',3'-isopropylidene adenosine (362-75-4) + 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine (151359-36-3) + (R)-1-[(4R,5S)-5-(6-Amino-1-oxy-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol + 6-amino-4-(2,3-O-isopropylidene-D-ribofuranosylamino)-5-(N-methylamino)pyrimidine 1-oxide

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 25 ℃; for 25h;

DOI:10.1016/S0040-4020(97)10098-9

Reference yield: 28.0%

2',3'-O-(isopropylidene)-5'-O-(triphenylmethyl)uridine (10526-27-9) → 2',3'-isopropylidene adenosine (362-75-4) + 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine (151359-36-3) + (R)-1-[(4R,5S)-5-(6-Amino-1-oxy-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol + 1-(O2,O3-isopropylidene-O5-trityl-β-D-ribofuranosyl)-dihydro-pyrimidine-2,4-dione (31281-46-6)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 25 ℃; for 24h;

DOI:10.1016/S0040-4020(97)10098-9

Reference yield: 28.0%

2'-deoxy-D-adenosine (958-09-8,7005-15-4) → 2',3'-isopropylidene adenosine (362-75-4) + 1-(Adenin-9-yl)-1,2-dideoxy-D-erythropentitol (84608-34-4) + 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine (151359-36-3) + (R)-1-[(4R,5S)-5-(6-Amino-1-oxy-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 25 ℃; for 24h;

DOI:10.1016/S0040-4020(97)10098-9

upstream raw materials:

2',3'-isopropylideneadenosine-1-oxide

2',3'-O-(isopropylidene)-5'-O-(triphenylmethyl)uridine

2'-deoxy-D-adenosine

adenosine

Downstream raw materials:

(+)-neplanocin A

9-(2S,3R)-erythro-(4-O-p-toluenesulfonyl-2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine

N-(9-{(4S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-9H-purin-6-yl)-benzamide

4-(6-amino-purin-9-yl)-2,3-dihydroxy-butyric acid