N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester

Base Information

• Chemical Name: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester
• CAS No.: 337903-73-8
• Molecular Formula: C₃₉H₄₂N₂O₁₃
• Molecular Weight: 746.768

Synonyms:N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester

Chemical Property of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester

Chemical Property:

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Technology Process of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester

There total 7 articles about N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine 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: 75.0%

acetic anhydride (108-24-7) + benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate (150631-07-5) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester (337903-73-8)

Guidance literature:

With zinc; for 14h;

DOI:10.1021/jo005712m

Reference yield: 64.0%

N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester (337903-73-8)

Guidance literature:

With mercury dibromide; In 1,2-dichloro-ethane; for 9h; Heating;

DOI:10.1016/S0008-6215(03)00071-5

Reference yield: 20.0%

N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-L-serine benzyl ester (1174725-59-7) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester (337903-73-8)

Guidance literature:

With mercury dibromide; In 1,2-dichloro-ethane; for 9h; Reflux;

DOI:10.1016/j.tet.2009.04.069

upstream raw materials:

acetic anhydride

benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate

N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester

N^α-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine

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