N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-alpha-D-galactopyranosyl]-L-serine pentafluorophenyl ester

Base Information

• Chemical Name: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-alpha-D-galactopyranosyl]-L-serine pentafluorophenyl ester
• CAS No.: 137816-29-6
• Molecular Formula: C38H35F5N2O13
• Molecular Weight: 822.694
• Mol file: 137816-29-6.mol

Synonyms:N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-alpha-D-galactopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-alpha-D-galactopyranosyl]-L-serine pentafluorophenyl ester

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-alpha-D-galactopyranosyl]-L-serine pentafluorophenyl ester

There total 6 articles about N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-alpha-D-galactopyranosyl]-L-serine 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: 75.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine (120173-57-1) → Nα-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine pentafluorophenyl ester (137816-29-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 0 ℃;

DOI:10.1016/S0040-4039(00)93429-4

Reference yield: 68.0%

acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) + Nα-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine pentafluorophenyl ester (141462-11-5) → Nα-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine pentafluorophenyl ester (137816-29-6)

Guidance literature:

With zinc; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/acs.joc.9b02396

Reference yield:

D-galactal (21193-75-9) → Nα-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine pentafluorophenyl ester (137816-29-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine

2.1: iron(III) chloride hexahydrate; sodium azide; dihydrogen peroxide

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.67 h / -15 °C / Inert atmosphere

3.2: 3 h / -15 - 20 °C / Inert atmosphere

4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

4.2: -20 °C / Inert atmosphere; Molecular sieve

5.1: zinc / tetrahydrofuran / Inert atmosphere

With pyridine; sodium azide; iron(III) chloride hexahydrate; dihydrogen peroxide; sodium hydride; zinc; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1021/acs.joc.9b02396

upstream raw materials:

2,3,4,5,6-pentafluorophenol

N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine

acetic anhydride

N^α-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine pentafluorophenyl ester