N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Base Information

Chemical Name:N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester
CAS No.:1323240-35-2
Molecular Formula:C₅₂H₅₈N₂O₂₂
Molecular Weight:1063.03
Hs Code.:

N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Synonyms:N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

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Chemical Property of N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

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Technology Process of N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

There total 8 articles about N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-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: 72.0%

: 125760-26-1
N-Fmoc serine phenacyl ester

: 126417-63-8
3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate

: 1323240-35-2
N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tet.2011.05.133

Reference yield:

: 1323240-19-2
1-methyl-1-cyclopropylmethyl 3,4,6-tri-O-benzyl-D-mannopyranoside

: 1323240-35-2
N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 0.75 h / 0 °C / Inert atmosphere; Molecular sieve

2: zinc / 8 h / 20 °C

3: 10% palladium hydroxide on charcoal; hydrogen / ethyl acetate / 20 °C / 2327.23 Torr / Autoclave

4: pyridine / 4 h / Cooling with ice

5: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere; Cooling with ice

7: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere; Molecular sieve

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 10% palladium hydroxide on charcoal; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; zinc; In dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2011.05.133

Reference yield:

: 1323240-27-2
1-methyl-1-cyclopropylmethyl [3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-benzyl-D-mannopyranoside

: 1323240-35-2
N-(9-fluorenylmethoxycarbonyl)-O-[[3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-L-serine phenacyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: zinc / 8 h / 20 °C

2: 10% palladium hydroxide on charcoal; hydrogen / ethyl acetate / 20 °C / 2327.23 Torr / Autoclave

3: pyridine / 4 h / Cooling with ice

4: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere; Cooling with ice

6: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere; Molecular sieve

With pyridine; 10% palladium hydroxide on charcoal; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; zinc; In dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2011.05.133