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

Base Information

• Chemical Name: N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester
• CAS No.: 273944-57-3
• Molecular Formula: C₃₅H₃₆N₄O₉
• Molecular Weight: 656.692

Synonyms:N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester

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

Chemical Property:

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

There total 8 articles about N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl 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: 82.0%

N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (273944-47-1) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (273944-57-3)

Guidance literature:

With thiourea; In N,N-dimethyl-formamide; at 70 ℃; for 1h;

DOI:10.1016/S0008-6215(99)00313-4

Reference yield:

Fmoc-Thr-OH (73731-37-0) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (273944-57-3)

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: 97 percent / aq. TFA / CH₂Cl₂ / 8 h / 0 °C

4.1: 87 percent / p-TsOH*H₂O / acetonitrile / 24 h / 20 °C

With N-Bromosuccinimide; tetrabutylammonium trifluoromethylsulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/ja015570t

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-L-threonine allyl ester (136523-92-7) → Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (273944-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / N-bromosuccinimide; tetrabutylammonium triflate / CH₂Cl₂ / -28 °C

2: 97 percent / aq. TFA / CH₂Cl₂ / 8 h / 0 °C

3: 87 percent / p-TsOH*H₂O / acetonitrile / 24 h / 20 °C

With N-Bromosuccinimide; tetrabutylammonium trifluoromethylsulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ja015570t

upstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester

Fmoc-Thr-OH

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

p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside

Downstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine allyl ester

N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine allyl ester

N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine

N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine

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