Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 477329-92-3
• Molecular Formula: C₄₇H₅₄N₁₂O₁₅
• Molecular Weight: 1027.02
• Mol file: 477329-92-3.mol

Synonyms:Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-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: 52.0%

2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl trichloroacetimidate (188913-44-2) + 1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (236115-80-3) → Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester (477329-92-3)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃; for 0.666667h;

DOI:10.1021/ol026588r

Reference yield:

Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester (477329-92-3) → (2S,3S,4R,5R,6S)-2-[(1R,2R,3S,5R,6S)-3,5-Diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 5h;

DOI:10.1021/ol026588r

Reference yield:

Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester (477329-92-3) → (2S,3S,4R,5R,6S)-2-[(1R,2R,3S,5R,6S)-3,5-Diamino-2-((2R,3R,4R,5S,6R)-3-amino-6-aminomethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-hydroxy-cyclohexyloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / methanol / 5 h / 20 °C

2: PMe₃; NaOH / tetrahydrofuran; H₂O / 2 h / 50 °C

3: H₂ / Pd(OH)2/C / acetic acid; H₂O / 24 h / 20 °C

With sodium hydroxide; hydrogen; potassium carbonate; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; methanol; water; acetic acid; 2: Staudinger reaction;

DOI:10.1021/ol026588r

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl trichloroacetimidate

1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine