N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Base Information

Chemical Name:N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester
CAS No.:1356032-75-1
Molecular Formula:C₅₅H₆₄F₂N₂O₁₅
Molecular Weight:1031.11
Hs Code.:

N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Synonyms:N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

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Chemical Property of N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

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Technology Process of N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

There total 4 articles about N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl 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: 65.0%

: 1373519-95-9
Fmoc-Thr-(β-2,6F-Bn2Gal-(1-3)-α-GalNAc)-OtBu

: 108-24-7
acetic anhydride

: 1356032-75-1
N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Guidance literature:: With pyridine; at 20 ℃; for 20h;
DOI:10.1039/c1cc15139h

Reference yield:

: 3,4-di-O-benzyl-2,6-dideoxy-2,6-fluoro-D-galactopyranose

: 1356032-75-1
N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 16 h / 0 - 20 °C

2.1: dichloromethane / 1 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 20 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

3.1: NaHSO₄-SiO₂ / methanol; dichloromethane / 18 h / 20 °C

4.1: pyridine / 20 h / 20 °C

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; 2.1: Schmidt reaction / 2.2: Schmidt reaction;
DOI:10.1039/c1cc15139h

Reference yield:

: 1356032-70-6
3,4-di-O-benzyl-2,6-dideoxy-2,6-fluoro-α-D-galactopyranosyl trichloroacetimidate

: 1356032-75-1
N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[3,4-tri-O-benzyl-2,6-dideoxy-2,6-difluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: dichloromethane / 1 h / 20 °C / Inert atmosphere; Molecular sieve

1.2: 20 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

2.1: NaHSO₄-SiO₂ / methanol; dichloromethane / 18 h / 20 °C

3.1: pyridine / 20 h / 20 °C

With pyridine; In methanol; dichloromethane; 1.1: Schmidt reaction / 1.2: Schmidt reaction;
DOI:10.1039/c1cc15139h