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

Base Information

Chemical Name:Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester
CAS No.:183660-34-6
Molecular Formula:C₅₃H₆₀N₄O₁₇
Molecular Weight:1025.08
Hs Code.:

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

Synonyms:Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

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Chemical Property of Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

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Technology Process of Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

There total 4 articles about Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl 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: 76.0%

: 106-95-6
allyl bromide

: 183660-32-4
Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-((1R,2S,3S,4R,6S)-3-acetoxy-4,6-bis-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy)-5-benzyloxycarbonylamino-2-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-4-yl ester

: 183660-34-6
Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

Guidance literature:: With tetra-(n-butyl)ammonium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; dimethyl sulfoxide; for 0.5h; Ambient temperature;
DOI:10.1021/ja9612817

Reference yield:

: 119-04-0
neomycin B

: 183660-34-6
Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / conc. aq. HCl / methanol / 6 h / Heating

2: 86 percent / aq. NaHCO₃ / acetone; toluene / 4 °C

3: 78 percent / pyridine / dimethylformamide / Ambient temperature

4: 76 percent / n-Bu₄NI, (Me₃Si)2NLi / dimethylsulfoxide; tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; hydrogenchloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja9612817

Reference yield:

: 22854-75-7
N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine

: 183660-34-6
Acetic acid (1S,2S,3R,4S,6R)-2-allyloxy-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / pyridine / dimethylformamide / Ambient temperature

2: 76 percent / n-Bu₄NI, (Me₃Si)2NLi / dimethylsulfoxide; tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; tetra-(n-butyl)ammonium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja9612817