N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

Base Information

Chemical Name:N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester
CAS No.:136831-27-1
Molecular Formula:C₄₈H₄₆N₂O₁₁
Molecular Weight:826.9
Hs Code.:

Synonyms:N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

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Chemical Property of N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

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Technology Process of N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

There total 10 articles about N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl 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: 80.8%

: N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

: 507-09-5
tiolacetic acid

: 136831-27-1
N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

Guidance literature:: In dichloromethane; for 48h; Ambient temperature;
DOI:10.1016/0008-6215(92)84163-M

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 136831-27-1
N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / p-TsOH*H₂O / acetonitrile / 1.5 h / Ambient temperature

2: 1) NaH / 1) THF, 60 deg C, 1 h; 2) THF, 60 deg C, overnight

3: 96.8 percent / AcOH, n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

4: 13.1 percent / diethylaminosulfur trifluoride / tetrahydrofuran / 0.5 h / Ambient temperature

5: 60.4 percent / Cp₂ZrCl₂, AgClO₄, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / -20 - -10 °C

6: 80.8 percent / CH₂Cl₂ / 48 h / Ambient temperature

With zirconocene dichloride; diethylamino-sulfur trifluoride; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/0008-6215(92)84163-M

Reference yield:

: 132183-13-2
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate

: 136831-27-1
N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 82.8 percent / imidazole / dimethylformamide / 2.5 h / 60 °C

2: NaOMe / methanol; toluene / 3 h / Ambient temperature

3: 91 percent / p-TsOH*H₂O / acetonitrile / 1.5 h / Ambient temperature

4: 1) NaH / 1) THF, 60 deg C, 1 h; 2) THF, 60 deg C, overnight

5: 96.8 percent / AcOH, n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

6: 13.1 percent / diethylaminosulfur trifluoride / tetrahydrofuran / 0.5 h / Ambient temperature

7: 60.4 percent / Cp₂ZrCl₂, AgClO₄, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / -20 - -10 °C

8: 80.8 percent / CH₂Cl₂ / 48 h / Ambient temperature

With 1H-imidazole; zirconocene dichloride; diethylamino-sulfur trifluoride; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silver perchlorate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/0008-6215(92)84163-M