N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine

Base Information

• Chemical Name: N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine
• CAS No.: 1453118-09-6
• Molecular Formula: C₂₂H₃₁N₅O₉
• Molecular Weight: 509.516
• Mol file: 1453118-09-6.mol

Synonyms:N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine

Chemical Property of N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine

There total 5 articles about N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine 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: 81.0%

C22H31ClN2O9 (1453118-07-4) → N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine (1453118-09-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 240h; Inert atmosphere;

DOI:10.1002/ejoc.201300236

Reference yield:

N-[(1R,2S,4S,5S)-2-(3-acetoxybenzamido)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine (1453118-05-2) → N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine (1453118-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / methanol / 0.25 h / 20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 240 h / 50 °C / Inert atmosphere

With sodium azide; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300236

Reference yield:

3-acetoxybenzoic acid (6304-89-8) → N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-azidoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine (1453118-09-6)

Guidance literature:

Multi-step reaction with 3 steps

1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

2: sodium methylate / methanol / 0.25 h / 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 240 h / 50 °C / Inert atmosphere

With sodium azide; sodium methylate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300236

upstream raw materials:

C₂₂H₃₁ClN₂O₉

3-acetoxybenzoic acid

N-[(1R,2S,4S,5S)-2-(benzyloxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine

N-[(1R,2S,4S,5S)-2-(3-acetoxybenzamido)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine

Downstream raw materials:

N-[(1R,2S,4S,5S)-2-(3-hydroxybenzamido)-4-(2-aminoethoxy)-5-hydroxycyclohexanecarboxyl]-α-L-fucopyranosylamine

C₁₀₅H₁₄₄N₂₀O₄₀