9-(2,3-Anhydro-.beta.-D-ribofuranosyl)-Adenine

Base Information

• Chemical Name: 9-(2,3-Anhydro-.beta.-D-ribofuranosyl)-Adenine
• CAS No.: 2627-64-7
• Molecular Formula: C10H11 N5 O3
• Molecular Weight: 249.229
• Mol file: 2627-64-7.mol

Synonyms:3,6-Dioxabicyclo[3.1.0]hexane,adenosine deriv.; 2',3'-Anhydroadenosine; 9-(2',3'-Anhydro-b-D-ribofuranosyl)adenine

Chemical Property of 9-(2,3-Anhydro-.beta.-D-ribofuranosyl)-Adenine

Chemical Property:

• Vapor Pressure: 7.8E-15mmHg at 25°C
• Boiling Point: 591.4°Cat760mmHg
• Flash Point: 311.5°C
• Density: 2.23g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9-(2,3-Anhydro-.beta.-D-ribofuranosyl)-Adenine

There total 3 articles about 9-(2,3-Anhydro-.beta.-D-ribofuranosyl)-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: 98.0%

adenosine (58-61-7) → 2',3'-dehydroadenosine (2627-64-7,4336-89-4,40110-98-3)

Guidance literature:

With acetoxyisobutyryl bromide; In water; acetonitrile; at 20 ℃; for 1h;

Reference yield: 60.0%

Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ4-furo[3,2-d][1,3,2]dioxathiin-7-yl ester (669055-55-4) → 9-(2,3-anhydro-β-D-ribofuranosyl)adenine (2627-64-7) + 9-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]adenine (125084-71-1)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; for 264h;

DOI:10.1016/j.tetlet.2003.10.092

Reference yield:

→ 2',3'-dehydroadenosine (2627-64-7,4336-89-4,40110-98-3)

Guidance literature:

3/4,CH3OH,NH3;

DOI:10.1021/ja00441a053

upstream raw materials:

Benzyl-carbamic acid (4aR,6R,7R,7aS)-6-(6-amino-purin-9-yl)-2-oxo-tetrahydro-2λ⁴-furo[3,2-d][1,3,2]dioxathiin-7-yl ester

adenosine

Downstream raw materials:

(2R,3R,5S)-2-[6-(N-benzoylbenzamido)-9H-purin-9-yl]-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate

(2R,3R,5S)-2-[6-(N-benzoylbenzamido)-2-nitro-9H-purin-9-yl]-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate

3′-deoxyinosine

(2R,3R,5S)-5-(hydroxymethyl)-2-(9H-purin-9-yl)tetrahydrofuran-3-ol

Refernces

• 1、 Takatsuki, Ken-Ichi,Yamamoto, Makoto,Ohgushi, Sumito,Kohmoto, Shigeo,Kishikawa, Keiki,Yamashita, Haruhiro. "A new protecting group '3′,5′-O-sulfinyl' for xylo-nucleosides. A simple and efficient synthesis of 3′-amino-3′-deoxyadenosine (a puromycin intermediate), 2,2′-anhydro-pyrimidine nucleosides and 2′,3′-anhydro-adenosine". . p. 137 - 140. Retrieved 2007/10/03.