Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 228394-77-2
• Molecular Formula: C₆₀H₆₆N₆O₁₃Si
• Molecular Weight: 1107.3

Synonyms:Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

There total 8 articles about Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-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:

2-N-acetyl-6-O-(diphenylcarbamoyl)guanine (146558-05-6) + Benzoic acid (2S,3R,4R,5R)-2-acetoxy-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (228394-76-1) → Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (228394-77-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In toluene; at 80 ℃; for 3h; Yield given;

DOI:10.1021/ja990274q

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (228394-77-2)

Guidance literature:

Multi-step reaction with 7 steps

1: HCl / CH₂Cl₂ / 2 h / 0 °C

2: CH₂Cl₂ / 18 h

3: NaOCH₃, CH₃OH / 2 h

4: pyridine, Et₃N / CH₂Cl₂ / 4 h

5: IDCP / 1,2-dichloro-ethane; diethyl ether / 3 h

6: 15 h

7: TMSOTf / toluene / 3 h / 80 °C

With pyridine; hydrogenchloride; methanol; iodonium(di-γ-collidine) perchlorate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; triethylamine; In diethyl ether; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ja990274q

Reference yield:

N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → Benzoic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester (228394-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,2-dichloro-ethane / 0.25 h / 80 °C

2: TMSOTf / toluene / 3 h / 80 °C

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; toluene;

DOI:10.1021/ja990274q

upstream raw materials:

2-N-acetyl-6-O-(diphenylcarbamoyl)guanine

Benzoic acid (2S,3R,4R,5R)-2-acetoxy-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

Downstream raw materials:

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

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

Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

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

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