N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester

Base Information

• Chemical Name: N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester
• CAS No.: 384346-85-4
• Molecular Formula: C51H58N2O19
• Molecular Weight: 1003.02
• Mol file: 384346-85-4.mol

Synonyms:N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester;N-FMoc-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-Fmoc-4,6-benzylidene-2’’’’tetra-O-acetyl T Epitope, Threonyl Allyl Ester

Chemical Property of N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester

Chemical Property:

• PSA: 261.29000
• LogP: 4.88480
• Solubility.: Dichloromethane

Purity/Quality:

80%，90%，95%，98%，99% ^*data from raw suppliers

N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetylTEpitope,ThreonylAllylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester

There total 12 articles about N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl 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: 86.0%

tiolacetic acid (507-09-5) + Nα-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 (384346-84-3) → Nα-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 (384346-85-4)

Guidance literature:

With pyridine; at 20 ℃; for 8h;

DOI:10.1021/ja015570t

Reference yield:

Fmoc-Thr-OH (73731-37-0) → Nα-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 (384346-85-4)

Guidance literature:

Multi-step reaction with 6 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

5.1: 59 percent / silver triflate / toluene; CH₂Cl₂ / 1 h / -25 °C

6.1: 86 percent / pyridine / 8 h / 20 °C

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

DOI:10.1021/ja015570t

Reference yield:

Nα-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester → Nα-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 (384346-85-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / p-TsOH*H₂O / acetonitrile / 24 h / 20 °C

2: 59 percent / silver triflate / toluene; CH₂Cl₂ / 1 h / -25 °C

3: 86 percent / pyridine / 8 h / 20 °C

With pyridine; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja015570t

upstream raw materials:

tiolacetic acid

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

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

benzaldehyde dimethyl acetal

Downstream raw materials:

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

Refernces