(2R, 4R)-4-AMINOTETRAHYDROFURAN-2-METHANOL

Base Information

• Chemical Name: (2R, 4R)-4-AMINOTETRAHYDROFURAN-2-METHANOL
• CAS No.: 127682-80-8
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 117.148
• Mol file: 127682-80-8.mol

Synonyms:

Chemical Property of (2R, 4R)-4-AMINOTETRAHYDROFURAN-2-METHANOL

Chemical Property:

Purity/Quality:

((2R,4R)-4-AMINOTETRAHYDROFURAN-2-YL)METHANOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R, 4R)-4-AMINOTETRAHYDROFURAN-2-METHANOL

There total 12 articles about (2R, 4R)-4-AMINOTETRAHYDROFURAN-2-METHANOL 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:

((2S,4S)-4-Azido-tetrahydro-furan-2-yl)-methanol → (2R-cis)-4-aminotetrahydro-2-furanmethanol (127682-80-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 3h; Yield given; Ambient temperature;

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-aminotetrahydro-2-furanmethanol (127682-80-8)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jm00091a001

Reference yield:

(3R,5S)-5-Dimethoxymethyl-tetrahydro-furan-3-ol (127682-76-2) → (2R-cis)-4-aminotetrahydro-2-furanmethanol (127682-80-8)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jm00091a001

upstream raw materials:

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

(2R,4S)-4-hydroxy-2-dimethoxymethyltetrahydrofuran

(2R-trans)-tetrahydro-4-[[(4-methylphenyl)-sulfonyl]oxy]-2-furanmethanol

2(R)-<(dimethoxy)methyl>-4(S)-tetrahydrofuran

Downstream raw materials:

(2R-cis)-4-(6-chloro-9H-purin-9-yl)tetrahydrofuran-2-methanol

(2R-cis)-4-(6-chloro-9H-purin-9-yl)-tetrahydro-2-furanmethanol

IsoddA

{(2R,4R)-4-[2-Amino-6-chloro-5-(4-chloro-phenylazo)-pyrimidin-4-ylamino]-tetrahydro-furan-2-yl}-methanol

Refernces

• 1、 Huryn,Sluboski,Tam,Weigele,Sim,Anderson,Mitsuya,Broder. "Synthesis and anti-HIV activity of isonucleosides". . p. 2347 - 2354. Retrieved 2007/10/02.