N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester

Base Information

• Chemical Name: N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester
• CAS No.: 162894-85-1
• Molecular Formula: C₃₉H₃₃F₅N₂O₁₄S₂
• Molecular Weight: 912.82

Synonyms:N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester

Chemical Property of N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester

There total 5 articles about N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl 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: 85.0%

Nα-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (86061-06-5) + Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-6-bromo-5-(3,5-dioxo-[1,2,4]dithiazolidin-4-yl)-tetrahydro-pyran-4-yl ester → Nα-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester (162894-85-1)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1021/ja953529i

Reference yield: 71.0%

Nα-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (86061-06-5) + O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl) trichloroacetimidate (162894-83-9) → Nα-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester (162894-85-1)

Guidance literature:

With AgOTfl; In dichloromethane; Ambient temperature;

DOI:10.1039/P19950000405

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-(dithiasuccinoylamino)-D-β-glucopyranosyl bromide (162894-81-7) → Nα-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester (162894-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 88.5 percent / acetone; H₂O / 3 h

2: 67 percent / K₂CO₃, molecular sieves 3A / CH₂Cl₂ / Ambient temperature

3: 71 percent / AgOTfl / CH₂Cl₂ / Ambient temperature

With 3 A molecular sieve; potassium carbonate; In dichloromethane; water; acetone;

DOI:10.1039/P19950000405

upstream raw materials:

N^α-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester

O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl) trichloroacetimidate

3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranose

3,4,6-tri-O-acetyl-2-deoxy-2-(dithiasuccinoylamino)-D-β-glucopyranosyl bromide

Downstream raw materials:

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester

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