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

Base Information

• Chemical Name: 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
• CAS No.: 228394-76-1
• Molecular Formula: C₄₂H₅₄O₁₂Si
• Molecular Weight: 778.969

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 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)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ja990274q

Reference yield:

(2S,3aR,5R,6R,6aR)-2-Ethoxy-5-hydroxymethyl-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol → 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)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine, Et₃N / CH₂Cl₂ / 4 h

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

3: 15 h

With pyridine; iodonium(di-γ-collidine) perchlorate; triethylamine; In diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ja990274q

Reference yield:

(2S,3aR,5R,6R,6aR)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-ethoxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 15 h

With iodonium(di-γ-collidine) perchlorate; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1021/ja990274q

upstream raw materials:

acetic acid

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

2,3,5-tri-O-benzoyl-α-D-ribofuranose

Downstream raw materials:

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

2-Amino-9-[(2R,3R,4S,5R)-4-((2S,3S,4R,5R,6S)-3,4-bis-benzyloxy-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one

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

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

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