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

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Chemical Name:N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester
CAS No.:136831-28-2
Molecular Formula:C₄₁H₄₂N₂O₁₁
Molecular Weight:738.791
Hs Code.:

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

There total 9 articles about N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-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: 88.6%

: 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

: 136831-28-2
N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

Guidance literature:: With acetic acid; In chloroform; at 60 ℃; for 3.5h;
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

: 136831-28-2
N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

Guidance literature:: Multi-step reaction with 9 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

9: 88.6 percent / 80percent aq. AcOH / CHCl₃ / 3.5 h / 60 °C

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; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/0008-6215(92)84163-M

Reference yield:

: 132183-15-4
tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-galactopyranoside

: 136831-28-2
N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 88.6 percent / 80percent aq. AcOH / CHCl₃ / 3.5 h / 60 °C

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; chloroform; acetonitrile;
DOI:10.1016/0008-6215(92)84163-M