[(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
• CAS No.: 87009-66-3
• Molecular Formula: C₃₈H₄₆F₂N₄O₉
• Molecular Weight: 740.801

Synonyms:

Chemical Property of [(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property:

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Safty Information:

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Useful:

Technology Process of [(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

There total 3 articles about [(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl 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:

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-de(methoxy)-3-oxo-sporaricin B (83866-00-6) → [(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (87009-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.) 0.25 M barium hydroxide; 2.) triethylamine / 1.) 1,4-dioxane, water, 1.5 h, 80 deg C; 2.) oxolane, 2 d, 37 deg C

With barium dihydroxide; diethylamino-sulfur trifluoride; triethylamine; In dichloromethane;

DOI:10.1016/0008-6215(83)88117-8

Reference yield:

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-de(O-methyl)sporaricin B (81090-88-2,81131-62-6,83916-87-4) → [(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (87009-66-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Heating

2: 72 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.) 0.25 M barium hydroxide; 2.) triethylamine / 1.) 1,4-dioxane, water, 1.5 h, 80 deg C; 2.) oxolane, 2 d, 37 deg C

With barium dihydroxide; diethylamino-sulfur trifluoride; triethylamine; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/0008-6215(83)88117-8

Reference yield:

Cbz-Gly-ONSuc (2899-60-7) + 1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3,3-difluoro-3-de(methoxy)sporaricin B (83866-01-7) → [(2R,3R,6S)-2-((1R,2R,3S,6R)-6-Benzyloxycarbonylamino-4,4-difluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-6-((R)-1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (87009-66-3) + 1,2',6'-tris(N-benzyloxycarbonyl)-4-N-(N-benzyloxycarbonylglycyl)-3,3-difluoro-3-de(methoxy)sporaricin B (87009-65-2)

Guidance literature:

With barium dihydroxide; triethylamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) 1,4-dioxane, water, 1.5 h, 80 deg C; 2.) oxolane, 2 d, 37 deg C;

DOI:10.1016/0008-6215(83)88117-8

upstream raw materials:

Cbz-Gly-ONSuc

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3,3-difluoro-3-de(methoxy)sporaricin B

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-de(methoxy)-3-oxo-sporaricin B

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-de(O-methyl)sporaricin B

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