N^α-(9-fluorenylmethoxycarbonyl)-N^γ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-L-asparagine tert-butyl ester

Base Information

• Chemical Name: N^α-(9-fluorenylmethoxycarbonyl)-N^γ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-L-asparagine tert-butyl ester
• CAS No.: 622830-67-5
• Molecular Formula: C₇₃H₈₆N₄O₁₉
• Molecular Weight: 1323.5

Synonyms:

Chemical Property of N^α-(9-fluorenylmethoxycarbonyl)-N^γ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-L-asparagine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of N^α-(9-fluorenylmethoxycarbonyl)-N^γ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-L-asparagine tert-butyl ester

There total 8 articles about N^α-(9-fluorenylmethoxycarbonyl)-N^γ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-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:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) → Nα-(9-fluorenylmethoxycarbonyl)-Nγ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-L-asparagine tert-butyl ester (622830-67-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -40 - 20 °C

2.1: 87 percent / TBAF; AcOH / tetrahydrofuran / 72 h / 0 - 20 °C

3.1: 85 percent / CuBr₂; 4 Angstroem molecular sieves; Bu₄NBr / CH₂Cl₂; dimethylformamide / 20 °C

4.1: ethylenediamine / butan-1-ol / 90 °C

4.2: pyridine / 20 °C

4.3: 86 percent / NaOMe / methanol / 3 h / 20 °C

5.1: H₂ / Lindlar catalyst / methanol / 2.5 h / 20 °C

6.1: 132 mg / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; silver trifluoromethanesulfonate; acetic acid; ethylenediamine; copper(ll) bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jo034773s

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → Nα-(9-fluorenylmethoxycarbonyl)-Nγ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-L-asparagine tert-butyl ester (622830-67-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aq. HBr; AcOH / CH₂Cl₂ / 4 h / 20 °C

2.1: 75 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -40 - 20 °C

3.1: 87 percent / TBAF; AcOH / tetrahydrofuran / 72 h / 0 - 20 °C

4.1: 85 percent / CuBr₂; 4 Angstroem molecular sieves; Bu₄NBr / CH₂Cl₂; dimethylformamide / 20 °C

5.1: ethylenediamine / butan-1-ol / 90 °C

5.2: pyridine / 20 °C

5.3: 86 percent / NaOMe / methanol / 3 h / 20 °C

6.1: H₂ / Lindlar catalyst / methanol / 2.5 h / 20 °C

7.1: 132 mg / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen bromide; hydrogen; silver trifluoromethanesulfonate; acetic acid; ethylenediamine; copper(ll) bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jo034773s

Reference yield:

O-(2,3,4-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (622830-64-2) → Nα-(9-fluorenylmethoxycarbonyl)-Nγ-[O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-L-asparagine tert-butyl ester (622830-67-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / CuBr₂; 4 Angstroem molecular sieves; Bu₄NBr / CH₂Cl₂; dimethylformamide / 20 °C

2.1: ethylenediamine / butan-1-ol / 90 °C

2.2: pyridine / 20 °C

2.3: 86 percent / NaOMe / methanol / 3 h / 20 °C

3.1: H₂ / Lindlar catalyst / methanol / 2.5 h / 20 °C

4.1: 132 mg / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; tetrabutylammomium bromide; hydrogen; ethylenediamine; copper(ll) bromide; Lindlar's catalyst; In methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jo034773s

upstream raw materials:

FmocAsp(OBt)OBu^t

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

Fmoc-Asp-O-t-Bu

Downstream raw materials:

C₅₄H₇₄N₆O₁₉

C₄₁H₅₆F₅N₇O₂₁

C₅₈H₇₉N₇O₂₁

C₆₉H₈₄N₆O₂₁

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