N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine

Base Information

• Chemical Name: N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine
• CAS No.: 384346-83-2
• Molecular Formula: C₄₀H₅₀N₂O₁₀Si
• Molecular Weight: 746.93

Synonyms:N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine

Chemical Property of N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine

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Technology Process of N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine

There total 8 articles about N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine 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: 85.0%

Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (384346-82-1) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine (384346-83-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ja015570t

Reference yield:

Fmoc-Thr-OH (73731-37-0) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine (384346-83-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. CsCO₃ / ethanol / pH 7

1.2: 90 percent / dimethylformamide / 3.5 h / 0 - 20 °C

2.1: 50 percent / N-bromosuccinimide; tetrabutylammonium triflate / CH₂Cl₂ / -28 °C

3.1: 80 percent / pyridine / 4 h / 20 °C

4.1: 85 percent / N-methylaniline; (PPh₃)4Pd⁽⁰⁾ / tetrahydrofuran / 1 h / 20 °C

With pyridine; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammonium trifluoromethylsulfonate; N-methylaniline; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja015570t

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine (384346-83-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / p-TsOH*H₂O / acetonitrile / 2 h / 20 °C

2: 93 percent / pyridine; DMAP / 24 h / 20 °C

3: 50 percent / N-bromosuccinimide; tetrabutylammonium triflate / CH₂Cl₂ / -28 °C

4: 80 percent / pyridine / 4 h / 20 °C

5: 85 percent / N-methylaniline; (PPh₃)4Pd⁽⁰⁾ / tetrahydrofuran / 1 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammonium trifluoromethylsulfonate; toluene-4-sulfonic acid; N-methylaniline; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja015570t

upstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester

benzaldehyde dimethyl acetal

Fmoc-Thr-OH

N-(9-fluorenylmethoxycarbonyl)-L-threonine allyl ester

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