Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester
• CAS No.: 344779-64-2
• Molecular Formula: C₄₄H₅₁N₃O₁₇
• Molecular Weight: 893.899

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-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: 46.0%

acetic anhydride (108-24-7) + [(1R,2S,3R,4R,5S)-5-Benzyloxycarbonylamino-4-((2S,3R,4R,5S,6R)-3-benzyloxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2,3-dihydroxy-cyclohexyl]-carbamic acid benzyl ester (23600-10-4) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester (344779-64-2)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00194-6

Reference yield: 43.0%

allyl bromide (106-95-6) + Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester (344779-64-2) → Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (344779-65-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; lithium hexamethyldisilazane; In N,N-dimethyl-formamide; at 20 ℃; for 1.25h;

DOI:10.1016/S0040-4020(01)00194-6

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-2-acetoxymethyl-5-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester (344779-64-2) → (2R,3S,4R,5R,6S)-5-Amino-6-{(1R,2R,3S,4R,6S)-4,6-diamino-2-[2-(2-amino-ethylamino)-ethoxy]-3-hydroxy-cyclohexyloxy}-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Guidance literature:

Multi-step reaction with 5 steps

1.1: 43 percent / tetrabutylammonium isodide; LiHMDS / dimethylformamide / 1.25 h / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 84 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

3.1: 66 percent / NaBH₃CN / methanol; acetic acid; tetrahydrofuran / 20 °C

4.1: NaOMe / methanol; tetrahydrofuran / 3 h / 20 °C

5.1: H₂ / Pd/C / H₂O; dioxane; acetic acid / 3 h / 20 °C / 760 Torr

With hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium cyanoborohydride; ozone; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00194-6

upstream raw materials:

acetic anhydride

[(1R,2S,3R,4R,5S)-5-Benzyloxycarbonylamino-4-((2S,3R,4R,5S,6R)-3-benzyloxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2,3-dihydroxy-cyclohexyl]-carbamic acid benzyl ester

Downstream raw materials:

Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

[(1R,2S,3R,4R,5S)-3-(2-Amino-ethoxy)-5-benzyloxycarbonylamino-4-((2S,3R,4R,5S,6R)-3-benzyloxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl]-carbamic acid benzyl ester

Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-2-(2-oxo-ethoxy)-cyclohexyl ester

Acetic acid (1S,2S,3R,4S,6R)-2-(2-azido-ethoxy)-4,6-bis-benzyloxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

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