benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate

Base Information

• Chemical Name: benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate
• CAS No.: 337903-51-2
• Molecular Formula: C₆₀H₅₁NO₁₄
• Molecular Weight: 1010.06

Synonyms:benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate

Chemical Property of benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate

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Technology Process of benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate

There total 2 articles about benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate 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: 82.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8) → benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate (337903-51-2) + C40H43NO14(C5H2)4

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1021/jo005712m

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) → benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate (337903-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / HBr / CH₂Cl₂; acetic acid / 0 - 20 °C

2: 82 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂ / 12 h / 0 °C

With 4 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; In dichloromethane; acetic acid; 2: Koenigs-Knorr reaction;

DOI:10.1021/jo005712m

Reference yield: 97.0%

benzyl N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-threoninate (337903-51-2) → N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-threonine

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 1h;

DOI:10.1021/jo005712m

upstream raw materials:

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

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

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

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