N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Base Information

• Chemical Name: N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester
• CAS No.: 343309-00-2
• Molecular Formula: C₅₉H₄₄F₅NO₁₄
• Molecular Weight: 1085.99

Synonyms:N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property of N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property:

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Technology Process of N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester

There total 3 articles about N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl 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: 91.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-L-serine pentafluorophenyl ester (291311-49-4) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester (343309-00-2)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 3h;

DOI:10.1021/jo001584q

Reference yield:

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester (343309-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / HBr / acetic acid; acetic anhydride / 4.5 h / 50 °C

2: 91 percent / AgOTf; powdered molecular sieves 3 Angstrem / CH₂Cl₂ / 3 h / -30 °C

With 3 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; In dichloromethane; acetic anhydride; acetic acid;

DOI:10.1021/jo001584q

Reference yield:

benzoyl chloride (98-88-4) → Nα-(fluoren-9-ylmethoxycarbonyl)-Nα-methyl-3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]-L-serine pentafluorophenyl ester (343309-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 4-(dimethylamino)pyridine; pyridine / 18 h

2: 97 percent / HBr / acetic acid; acetic anhydride / 4.5 h / 50 °C

3: 91 percent / AgOTf; powdered molecular sieves 3 Angstrem / CH₂Cl₂ / 3 h / -30 °C

With pyridine; dmap; 3 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; In dichloromethane; acetic anhydride; acetic acid;

DOI:10.1021/jo001584q

upstream raw materials:

2,3,4,6-tetra-O-benzoylglucosyl bromide

N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside

benzoyl chloride

Downstream raw materials:

N^α-acetyl-L-alanyl-N^α-methyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-seryl-L-phenylalanine amide

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