Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester
• CAS No.: 1053741-58-4
• Molecular Formula: C₃₈H₅₈N₄O₁₅Si
• Molecular Weight: 838.982

Synonyms:Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

There total 12 articles about Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-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:

C52H84N6O17Si → Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester (1053741-58-4)

Guidance literature:

C₅₂H₈₄N₆O₁₇Si; With 4-methyl-morpholine; phenyl isothiocyanate; at 20 ℃; for 0.5h; pH=8 - 9;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 30h; Further stages.;

DOI:10.1016/j.tetlet.2004.02.032

Reference yield:

C66H94N8O17S2Si (1053637-14-1) → Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester (1053741-58-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200500382

Reference yield:

{(1-Ethyl-propyl)-[2-(1-ethyl-propylamino)-acetyl]-amino}-acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester (1053380-79-2) → Benzoic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-{(2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1-ethyl-propylamino)-acetoxymethyl]-tetrahydro-pyran-4-yloxy}-6-acetoxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester (1053741-58-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 114 mg / aq. NaHCO₃ / 0.5 h / 20 °C

2: 89 percent / NIS; TfOH / CH₂Cl₂ / 2 h / -40 °C

3: TFA / CH₂Cl₂ / 0.5 h / 20 °C

4: NMM / dimethylformamide / 0.5 h / 20 °C

5: TFA / CH₂Cl₂ / 0.5 h / 20 °C

With 4-methyl-morpholine; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200500382

upstream raw materials:

C₆₆H₉₄N₈O₁₇S₂Si

C₅₆H₈₉N₉O₁₀S₂Si

{(1-Ethyl-propyl)-[2-(1-ethyl-propylamino)-acetyl]-amino}-acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

tert-butyldimethylsilyl 4-O-acetyl-2-azido-2-deoxy-6-O-{[{2-[tert-butoxycarbonyl(1-ethylpropyl)amino]acetyl}(1-ethylpropyl)amino]acetyl}-β-D-galactopyranoside

Downstream raw materials:

tert-butyldimethylsilyl O-(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-6-O-{[tert-butoxycarbonyl(1-ethylpropyl)amino]acetyl}-2-deoxy-β-D-galactopyranoside

tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

benzoic acid 4,5-diacetoxy-2-[3-acetoxy-5-azido-2-{[tert-butoxycarbonyl-(1-ethyl-propyl)-amino]-acetoxymethyl}-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-4-yloxy]-6-acetoxymethyl-tetrahydro-pyran-3-yl ester

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