N-Fmoc-O-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine Allyl Ester

Base Information

• Chemical Name: N-Fmoc-O-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine Allyl Ester
• CAS No.: 301843-65-2
• Molecular Formula: C30H36N2O10
• Molecular Weight: 584.61424
• Mol file: 301843-65-2.mol

Synonyms:N-Fmoc-O-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine Allyl Ester;O-[2-(AcetylaMino)-2-deoxy-α-D-galactopyranosyl]-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-threonine 2-Propen-1-yl Ester

Chemical Property of N-Fmoc-O-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine Allyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 871.691°C at 760 mmHg
• PKA: 10.02±0.46(Predicted)
• Flash Point: 480.981°C
• PSA: 172.88000
• Density: 1.374g/cm³
• LogP: 1.75350
• Solubility.: Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

O-[2-Acetamido-2-deoxy-a-D-galactopyranosyl]-N-Fmoc-L-threonine 2-propen-1-yl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A byproduct formed during the synthesis of T Epitope, Threonyl.

Technology Process of N-Fmoc-O-[2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine Allyl Ester

There total 8 articles about N-Fmoc-O-[2-acetamido-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: 83.0%

N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester → N-(9H-fluoren-9-ylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (301843-65-2)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(00)00588-3

Reference yield:

(2S,3R)-3-((4aR,6S,7R,8R,8aR)-7-Azido-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester → N-(9H-fluoren-9-ylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (301843-65-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Zn; AcOH / CH₂Cl₂ / 0.33 h / 20 °C

2: 868 mg / methanol / 0.5 h / 20 °C

3: 83 percent / aq. TFA / 3 h / 0 °C

With acetic acid; trifluoroacetic acid; zinc; In methanol; dichloromethane; 1: Reduction / 2: Acetylation / 3: Hydrolysis;

DOI:10.1016/S0040-4020(00)00588-3

Reference yield:

(2S,3R)-3-((4aR,6S,7R,8R,8aR)-7-Amino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester → N-(9H-fluoren-9-ylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester (301843-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 868 mg / methanol / 0.5 h / 20 °C

2: 83 percent / aq. TFA / 3 h / 0 °C

With trifluoroacetic acid; In methanol; 1: Acetylation / 2: Hydrolysis;

DOI:10.1016/S0040-4020(00)00588-3

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Fmoc-Thr-OH

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

6-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-aminobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

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