Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 180403-71-8
• Molecular Formula: C₁₈H₁₈N₈O₄
• Molecular Weight: 410.392
• Mol file: 180403-71-8.mol

Synonyms:Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 10 articles about Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester 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: 80.0%

Benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester (180403-69-4) → Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (180403-71-8)

Guidance literature:

With pyridine; hydrazine hydrate; acetic acid; In water; at 20 ℃; for 26h;

DOI:10.1016/0008-6215(96)00028-6

Reference yield:

N-trimethylsilanyl-N-(7-trimethylsilanyl-7H-purin-6-yl)-benzamide (18055-46-4) → Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (180403-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / tin(IV) chloride / 1,2-dichloro-ethane / 20 h / 20 °C

2: 80 percent / sodium azide / dimethylformamide / 96 h / 20 °C

3: 80 percent / hydrazine hydrate, pyridine, acetic acid / H₂O / 26 h / 20 °C

With pyridine; sodium azide; tin(IV) chloride; hydrazine hydrate; acetic acid; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(96)00028-6

Reference yield:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → Benzoic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3-azidomethyl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (180403-71-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / pyridine / 16 h / 0 °C

2: 98 percent / acetic acid / H₂O / 20 h / 20 °C

3: 1.) sodium metaperiodate, NaHCO₃, 2.) sodium borohydride / 1.) ethanol, water, 20 deg C, 4 h, 2.) ethanol, water, 20 deg C, 1 h

4: 85 percent / pyridine / 20 h / 20 °C

5: 80 percent / glacial acetic acid, sulfuric acid / 48 h / 20 °C

6: 70 percent / tin(IV) chloride / 1,2-dichloro-ethane / 20 h / 20 °C

7: 80 percent / sodium azide / dimethylformamide / 96 h / 20 °C

8: 80 percent / hydrazine hydrate, pyridine, acetic acid / H₂O / 26 h / 20 °C

With pyridine; sodium tetrahydroborate; sodium periodate; sodium azide; sulfuric acid; tin(IV) chloride; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(96)00028-6

upstream raw materials:

Benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester

N-trimethylsilanyl-N-(7-trimethylsilanyl-7H-purin-6-yl)-benzamide

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

benzoyl chloride

Downstream raw materials:

Benzoic acid (2S,3S,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2S,3R,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester