N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Base Information

• Chemical Name: N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester
• CAS No.: 248927-82-4
• Molecular Formula: C₇₅H₈₅N₃O₁₇Si
• Molecular Weight: 1328.6
• Mol file: 248927-82-4.mol

Synonyms:N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Chemical Property of N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

There total 8 articles about N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl 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: 86.0%

chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane (221325-35-5) + N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester (248927-81-3) → N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester (248927-82-4)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(99)00649-3

Reference yield:

chloro(α,α-dimethylbenzyl)dimethylsilane (118740-38-8) → N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester (248927-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / aq. KOH / methanol / 20 h / 20 °C

2: 61 percent / NH₄NO₃; (CF₃CO)2O / acetonitrile / -15 - 20 °C

3: 100 percent / oxalyl chloride; DMF / CH₂Cl₂ / 0 - 20 °C

4: 86 percent / imidazole / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; ammonium nitrate; potassium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Substitution / 2: Nitration / 3: Substitution / 4: Substitution;

DOI:10.1016/S0040-4020(99)00649-3

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-L-threonine allyl ester (136523-92-7) → N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-6-O-(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester (248927-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / Cp₂ZrCl₂; AgClO₄; 4 Angstroem molecular sieves / CH₂Cl₂ / -40 - 20 °C

2: 100 percent / Zn; AcOH / tetrahydrofuran / 1 h / 20 °C

3: aq. CF₃COOH

4: 86 percent / imidazole / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; zirconocene dichloride; 4 A molecular sieve; silver perchlorate; acetic acid; trifluoroacetic acid; zinc; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Acetylation / 3: Substitution / 4: Substitution;

DOI:10.1016/S0040-4020(99)00649-3

upstream raw materials:

chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane

N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester

chloro(α,α-dimethylbenzyl)dimethylsilane

(α,α-dimethylbenzyl)dimethylsilanol