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

Base Information

• Chemical Name: 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
• CAS No.: 688315-52-8
• Molecular Formula: C₄₅H₆₈N₄O₁₈Si
• Molecular Weight: 981.136

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 15 articles about 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 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: 99.0%

acetic anhydride (108-24-7) + 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 (688315-48-2) → 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 (688315-52-8)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2004.02.032 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 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 (688315-52-8)

Guidance literature:

Multi-step reaction with 7 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

6: 83 mg / aq. NaHCO₃ / 0.5 h / 20 °C

7: 99 percent / pyridine / 2 h / 20 °C

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

DOI:10.1002/ejoc.200500382

Reference yield:

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) → 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 (688315-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 mg / aq. NaHCO₃ / 0.5 h / 20 °C

2: 99 percent / pyridine / 2 h / 20 °C

With pyridine; sodium hydrogencarbonate;

DOI:10.1002/ejoc.200500382

upstream raw materials:

acetic anhydride

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

C₅₆H₈₉N₉O₁₀S₂Si

C₆₆H₉₄N₈O₁₇S₂Si

Downstream raw materials:

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

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