1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxy-L-threo-pentitol

Base Information

• Chemical Name: 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxy-L-threo-pentitol
• CAS No.: 127682-82-0
• Molecular Formula: C₁₀H₁₁ClN₄O₂
• Molecular Weight: 254.676
• Mol file: 127682-82-0.mol

Synonyms:

Chemical Property of 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxy-L-threo-pentitol

Chemical Property:

• Vapor Pressure: 2.93E-10mmHg at 25°C
• Boiling Point: 486°C at 760 mmHg
• Flash Point: 247.7°C
• Density: 1.74g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxy-L-threo-pentitol

There total 17 articles about 1,4-anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxy-L-threo-pentitol 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: 48.0%

diethoxymethyl acetate (14036-06-7) + (2R-cis)-4-<(5-amino-6-chloro-4-pyrimidinyl)amino>tetrahydrofuran-2-methanol (127682-81-9) → (2R-cis)-4-(6-chloro-9H-purin-9-yl)tetrahydrofuran-2-methanol (127682-82-0)

Guidance literature:

at 100 ℃; for 120h;

DOI:10.1021/jm00091a001

Reference yield:

3-deoxy-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose 4-methylbenzenesufonate (3396-72-3) → (2R-cis)-4-(6-chloro-9H-purin-9-yl)tetrahydrofuran-2-methanol (127682-82-0)

Guidance literature:

Multi-step reaction with 8 steps

1: acetic acid / 72 h / 70 °C

2: pyridine / 15 h / 0 °C

3: CF₃COOH / dioxane / 5 h / 80 °C

4: NaBH₄ / dioxane / 0.5 h / Ambient temperature

5: NaN₃ / dimethylformamide / 5 h / 70 °C

6: H₂ / 10percent Pd/C / methanol / 3 h / Ambient temperature

7: 58 percent / triethylamine / 2-methyl-propan-2-ol / 72 h / Heating

8: 48 percent / 120 h / 100 °C

With pyridine; sodium tetrahydroborate; sodium azide; hydrogen; acetic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00091a001

Reference yield:

(3R,5S)-5-Dimethoxymethyl-tetrahydro-furan-3-ol (127682-76-2) → (2R-cis)-4-(6-chloro-9H-purin-9-yl)tetrahydrofuran-2-methanol (127682-82-0)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 15 h / 0 °C

2: CF₃COOH / dioxane / 5 h / 80 °C

3: NaBH₄ / dioxane / 0.5 h / Ambient temperature

4: NaN₃ / dimethylformamide / 5 h / 70 °C

5: H₂ / 10percent Pd/C / methanol / 3 h / Ambient temperature

6: 58 percent / triethylamine / 2-methyl-propan-2-ol / 72 h / Heating

7: 48 percent / 120 h / 100 °C

With pyridine; sodium tetrahydroborate; sodium azide; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00091a001

upstream raw materials:

diethoxymethyl acetate

(2R-cis)-4-[(5-amino-6-chloro-4-pyrimidinyl)-amino]tetrahydro-2-furanmethanol

3-deoxy-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose 4-methylbenzenesufonate

(2R-cis)-4-aminotetrahydro-2-furanmethanol

Downstream raw materials:

IsoddA

Refernces

• 1、 Huryn, Donna M.,Sluboski, Barbara C.,Tam, Steve Y,,Todaro, Luis J.,Weigele, Manfred. "SYNTHESYS OF ISO-DDA, MEMBER OF A NOVEL CLASS OF ANTI-HIV AGENTS". . p. 6259 - 6262. Retrieved 2007/10/02.