N²-(9-fluorenylmethoxycarbonyl)-N⁵-triphenylmethyl-L-glutaminyl-{N⁴-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester

Base Information

• Chemical Name: N²-(9-fluorenylmethoxycarbonyl)-N⁵-triphenylmethyl-L-glutaminyl-{N⁴-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester
• CAS No.: 383912-93-4
• Molecular Formula: C₅₅H₆₁N₅O₁₂
• Molecular Weight: 984.116

Synonyms:N²-(9-fluorenylmethoxycarbonyl)-N⁵-triphenylmethyl-L-glutaminyl-{N⁴-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester

Chemical Property of N²-(9-fluorenylmethoxycarbonyl)-N⁵-triphenylmethyl-L-glutaminyl-{N⁴-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester

Chemical Property:

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Technology Process of N²-(9-fluorenylmethoxycarbonyl)-N⁵-triphenylmethyl-L-glutaminyl-{N⁴-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester

There total 6 articles about N²-(9-fluorenylmethoxycarbonyl)-N⁵-triphenylmethyl-L-glutaminyl-{N⁴-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl 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: 100.0%

H2N-Asn(GlcNAc)-OtBu (288144-40-1) + Fmoc-Gln(Trt)-OBt (383913-00-6) → N2-(9-fluorenylmethoxycarbonyl)-N5-triphenylmethyl-L-glutaminyl-{N4-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester (383912-93-4)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 20 ℃;

DOI:10.1021/ol0101988

Reference yield:

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide (29847-23-2) → N2-(9-fluorenylmethoxycarbonyl)-N5-triphenylmethyl-L-glutaminyl-{N4-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester (383912-93-4)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C / 1-methyl-pyrrolidin-2-one / 4 h / 20 °C

2: 90 percent / 1-methyl-pyrrolidin-2-one / 20 °C

3: 100 percent / piperidine / 1-methyl-pyrrolidin-2-one / 0.67 h / 20 °C

4: 100 percent / 1-methyl-pyrrolidin-2-one / 20 °C

With piperidine; hydrogen; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one;

DOI:10.1021/ol0101988

Reference yield:

2-acetamido-2-deoxy-β-D-glucopyranosylamine (4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1) → N2-(9-fluorenylmethoxycarbonyl)-N5-triphenylmethyl-L-glutaminyl-{N4-[2-N-acetamido-2-deoxy-β-D-glucopyranosyl]}-L-asparagine tert-butyl ester (383912-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 1-methyl-pyrrolidin-2-one / 20 °C

2: 100 percent / piperidine / 1-methyl-pyrrolidin-2-one / 0.67 h / 20 °C

3: 100 percent / 1-methyl-pyrrolidin-2-one / 20 °C

With piperidine; In 1-methyl-pyrrolidin-2-one;

DOI:10.1021/ol0101988

upstream raw materials:

H₂N-Asn(GlcNAc)-OtBu

Fmoc-Gln(Trt)-OBt

2-acetamido-2-deoxy-β-D-glucopyranosylamine

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide

Downstream raw materials:

(S)-2-[(S)-2-(2-Acetylamino-acetylamino)-4-(trityl-carbamoyl)-butyrylamino]-N-((2R,3R,4R,5S,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-succinamic acid tert-butyl ester

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