1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: 1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester
• CAS No.: 345959-18-4
• Molecular Formula: C₁₇H₁₆N₂O₅
• Molecular Weight: 328.324

Synonyms:1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester

Chemical Property of 1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester

There total 3 articles about 1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic 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: 71.0%

bis-(p-nitrophenyl) carbonate (5070-13-3) + [(S)-5-Oxo-4-pyrrolidin-(2E)-ylidene-tetrahydro-furan-3-yl]-carbamic acid benzyl ester (345959-16-2) → 1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester (345959-18-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 96h;

DOI:10.1021/ol015848m

Reference yield:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (87219-29-2) → 1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester (345959-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 2.5 h / -78 °C

1.2: TMSCl / tetrahydrofuran / 0.17 h

1.3: 75 percent / bromine / tetrahydrofuran / 0.25 h

2.1: CH₂Cl₂ / 0.42 h / 90 °C

2.2: triphenylphosphine; triethylamine / CHCl₃ / 18 h / Heating

3.1: 71 percent / NaH / tetrahydrofuran / 96 h / 20 °C

With sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol015848m

Reference yield:

(2S,3S)-3-benzyloxycarbonylamino-2-bromo-1,4-butyrolactone (152251-80-4) → 1,5-dioxo-1,3,3a,6,7,8-hexahydro-2-oxa-4,5a-diaza-as-indacene-4-carboxylic acid benzyl ester (345959-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CH₂Cl₂ / 0.42 h / 90 °C

1.2: triphenylphosphine; triethylamine / CHCl₃ / 18 h / Heating

2.1: 71 percent / NaH / tetrahydrofuran / 96 h / 20 °C

With sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol015848m

upstream raw materials:

bis-(p-nitrophenyl) carbonate

[(S)-5-Oxo-4-pyrrolidin-(2E)-ylidene-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

(2S,3S)-3-benzyloxycarbonylamino-2-bromo-1,4-butyrolactone

Downstream raw materials:

C₄₈H₇₃N₅O₈Si

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