Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 228394-64-7
• Molecular Formula: C₄₆H₅₇N₅O₁₂Si
• Molecular Weight: 900.07
• Mol file: 228394-64-7.mol

Synonyms:Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl 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: 38.0%

Imidazole-1-carboxylic acid (3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester + {9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid benzyl ester (228394-63-6) → Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (228394-64-7) + Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (228394-65-8)

Guidance literature:

With zinc dibromide; In dichloromethane; for 1h; Heating;

DOI:10.1021/ja990274q

Reference yield:

2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine (72409-24-6) → Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (228394-64-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / KH, 18-crown-6 / tetrahydrofuran / 2 h

2: 94 percent / Bu₄NF / tetrahydrofuran / 20 h

3: 84 percent / imidazole / dimethylformamide / 2 h

4: 38 percent / ZnBr₂ / CH₂Cl₂ / 1 h / Heating

With 1H-imidazole; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hydride; zinc dibromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja990274q

Reference yield:

N-benzyloxycarbonylimidazole (22129-07-3) → Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (228394-64-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / KH, 18-crown-6 / tetrahydrofuran / 2 h

2: 94 percent / Bu₄NF / tetrahydrofuran / 20 h

3: 84 percent / imidazole / dimethylformamide / 2 h

4: 38 percent / ZnBr₂ / CH₂Cl₂ / 1 h / Heating

With 1H-imidazole; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hydride; zinc dibromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja990274q

upstream raw materials:

{9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid benzyl ester

2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine

N-benzyloxycarbonylimidazole

benzyl bromide

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester