[(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
• CAS No.: 67051-93-8
• Molecular Formula: C₄₃H₅₇N₅O₁₂
• Molecular Weight: 835.952

Synonyms:[(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property of [(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

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Technology Process of [(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

There total 5 articles about [(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(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: 54.0%

dimethylaminoacetic acid (1118-68-9) + 1,2',6'-tri-N-(benzyloxycarbonyl)fortimicin B (66962-55-8,71658-13-4,76822-42-9,78609-41-3,78781-05-2) → [(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (67051-93-8)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/S0008-6215(00)85134-4

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) → [(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (67051-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.05 g / methanol; H₂O / 1.) 3 h, 0 deg C, 2.) 22 h, RT

2: 54 percent / 1-hydroxybenzotriazole monohydrate, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 24 h / Ambient temperature

With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0008-6215(00)85134-4

Reference yield:

1,2',6',2''-tetra-N-benzyloxycarbonyl-4-N-methyl-fortimicin A (66962-56-9,71564-63-1,71873-76-2,73285-02-6,74742-44-2,76822-43-0,79703-12-1) → [(2R,3R,6S)-2-{(1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-5-[(2-dimethylamino-acetyl)-methyl-amino]-3,6-dihydroxy-4-methoxy-cyclohexyloxy}-6-(1-benzyloxycarbonylamino-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (67051-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.165 g / 5 percent aq. NaHCO₃ / methanol / 4 h / Heating

2: 54 percent / 1-hydroxybenzotriazole monohydrate, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 24 h / Ambient temperature

With sodium hydrogencarbonate; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol;

DOI:10.1016/S0008-6215(00)85134-4

upstream raw materials:

dimethylaminoacetic acid

1,2',6'-tri-N-(benzyloxycarbonyl)fortimicin B

N-(Benzyloxycarbonyloxy)succinimide

1,2',6',2''-tetra-N-benzyloxycarbonyl-4-N-methyl-fortimicin A

Downstream raw materials:

N-{(1S,2R,3R,4S,5S,6R)-4-Amino-3-[(2R,3R,6S)-3-amino-6-(1-amino-ethyl)-tetrahydro-pyran-2-yloxy]-2,5-dihydroxy-6-methoxy-cyclohexyl}-2-dimethylamino-N-methyl-acetamide; hydrochloride

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