O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester

Base Information

• Chemical Name: O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester
• CAS No.: 225663-02-5
• Molecular Formula: C₄₉H₅₂N₂O₁₁
• Molecular Weight: 844.959
• Mol file: 225663-02-5.mol

Synonyms:O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester

Chemical Property of O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester

There total 2 articles about O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine 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: 14.0%

N-[(9-fluorenyl)methoxycarbonyl]-L-serine tert-butyl ester (110797-35-8) + 3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester + O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester (225663-02-5)

Guidance literature:

With 3 A molecular sieve; potassium tert-butylate; In tetrahydrofuran; toluene; for 4h;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1167::AID-EJOC1167>3.0.CO;2-2

Reference yield:

1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranose → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester (225663-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / NEt₃ / CH₂Cl₂ / 0.33 h

2: 83 percent / molecular sieve (3 Angstroem), 1 M t-BuOK / toluene; tetrahydrofuran / 4 h

With 3 A molecular sieve; potassium tert-butylate; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1167::AID-EJOC1167>3.0.CO;2-2

Reference yield: 94.0%

O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serine tert-butyl ester (225663-02-5) → O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(fluorenyl-9-methoxycarbonyl)-L-serine tert-butyl ester (552888-49-0)

Guidance literature:

With Raney-Ni T₄/Pt; hydrogen; In ethanol; at 20 ℃; for 48h;

DOI:10.1002/ejoc.200390142

upstream raw materials:

N-[(9-fluorenyl)methoxycarbonyl]-L-serine tert-butyl ester

3,4,6-tri-O-benzyl-2-nitro-D-galactal

Downstream raw materials:

O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(fluorenyl-9-methoxycarbonyl)-L-serine tert-butyl ester

O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(fluorenyl-9-methoxycarbonyl)-L-serine

N-(fluorenyl-9-methoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-tert-butoxycarbonylamino-2-deoxy-α-D-galactopyranosyl)-L-serine