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

Base Information

Chemical Name:N-[(1R,2S,4S,5S)-2-(benzyloxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine
CAS No.:1453118-01-8
Molecular Formula:C₂₉H₃₉ClN₂O₁₂
Molecular Weight:643.088
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 1 articles about N-[(1R,2S,4S,5S)-2-(benzyloxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-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: 67.0%

: 1453117-99-1
N-[(1R,2S,4R,5S)-2-(benzyloxycarbonylamino)-4,5-epoxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine

: 107-07-3
2-chloro-ethanol

: 1453118-01-8
N-[(1R,2S,4S,5S)-2-(benzyloxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine

: 1453118-03-0
N-[(1R,2S,4R,5R)-2-(benzyloxycarbonylamino)-4-hydroxy-5-(2-chloroethoxy)cyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine

Guidance literature:: With copper(II) bis(trifluoromethanesulfonate); at 40 ℃; for 16h; Inert atmosphere;
DOI:10.1002/ejoc.201300236

Reference yield:

: 1453118-01-8
N-[(1R,2S,4S,5S)-2-(benzyloxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine

: C₂₁H₃₃ClN₂O₁₀

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In methanol; N,N-dimethyl-formamide; at 20 ℃; under 750.075 Torr; Inert atmosphere;
DOI:10.1002/ejoc.201300236

Reference yield:

: 1453118-01-8
N-[(1R,2S,4S,5S)-2-(benzyloxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexane]-2,3,4-tri-O-acetyl-α-L-fucopyranosylamine

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

Guidance literature:: Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen / methanol; N,N-dimethyl-formamide / 20 °C / 750.08 Torr / Inert atmosphere

2: 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

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

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

With sodium azide; palladium 10% on activated carbon; hydrogen; 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