(2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester

Base Information

• Chemical Name: (2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester
• CAS No.: 149636-43-1
• Molecular Formula: C₂₄H₃₅N₃O₁₂S₂
• Molecular Weight: 621.687

Synonyms:(2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester

Chemical Property of (2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester

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Technology Process of (2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester

There total 7 articles about (2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl 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: 86.0%

(2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (149665-63-4) → (2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (149636-43-1)

Guidance literature:

With potassium permanganate; acetic acid; at -10 ℃; for 1h;

DOI:10.1016/0040-4020(96)00197-4

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (149636-43-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / aq. NaOH / tetrahydrofuran / a) 0 deg C, 1 h, b) 20 deg C, 30 min

2: 40 percent / KHCO₃ / acetonitrile / 72 h / 80 °C

3: 92 percent / NaI / acetone / 24 h / 20 °C

4: 88 percent / POCl₃ / tetrahydrothiophene 1,1-dioxide; acetonitrile / 0.83 h / 70 °C

5: 35 percent / Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

6: 86 percent / aq. KMnO₄, aq. AcOH / 1 h / -10 °C

With sodium hydroxide; potassium permanganate; potassium hydrogencarbonate; acetic acid; triethylamine; sodium iodide; trichlorophosphate; In tetrahydrofuran; sulfolane; dichloromethane; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00197-4

Reference yield:

2-<2-N-(benzyloxycarbonyl)aminoethoxy>ethanol (145881-74-9) → (2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester (149636-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 percent / KHCO₃ / acetonitrile / 72 h / 80 °C

2: 92 percent / NaI / acetone / 24 h / 20 °C

3: 88 percent / POCl₃ / tetrahydrothiophene 1,1-dioxide; acetonitrile / 0.83 h / 70 °C

4: 35 percent / Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

5: 86 percent / aq. KMnO₄, aq. AcOH / 1 h / -10 °C

With potassium permanganate; potassium hydrogencarbonate; acetic acid; triethylamine; sodium iodide; trichlorophosphate; In sulfolane; dichloromethane; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00197-4

upstream raw materials:

(2S,5R,6R)-6-{2-[2-(2-Benzyloxycarbonylamino-ethoxy)-ethoxy]-ethanesulfonylamino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methoxymethyl ester

benzyl chloroformate

2-<2-N-(benzyloxycarbonyl)aminoethoxy>ethanol

2-<2-<2-N-(benzyloxycarbonyl)aminoethoxy>>-ethoxyethanesulfonyl chloride

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