(S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Base Information

Chemical Name:(S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane
CAS No.:236743-96-7
Molecular Formula:C₅₄H₆₆N₂O₉
Molecular Weight:887.126
Hs Code.:

Synonyms:(S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

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Chemical Property of (S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

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Technology Process of (S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

There total 5 articles about (S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane 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: 84.0%

: 15260-10-3
N-Boc-O-benzyl-L-threonine

: 236743-87-6
(S)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)-1-propyl amine

: 236743-96-7
(S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at -20 - 20 ℃; for 21h;
DOI:10.1016/S0968-0896(98)00245-4

Reference yield:

: 167990-42-3
3-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-propene

: 236743-96-7
(S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / MCPBA / CH₂Cl₂ / 11 h / Ambient temperature

2: NaN₃, NH₄Cl / ethanol; H₂O / 1.5 h / Heating

3: 18 percent / NaOH, Bu₄NHSO₄ / H₂O / 120 h / Ambient temperature

4: 86 percent / PPh₃, H₂O / tetrahydrofuran / 30 h / Ambient temperature

5: 84 percent / EDC, HOBT, NMM / dimethylformamide / 21 h / -20 - 20 °C

With 4-methyl-morpholine; sodium hydroxide; sodium azide; water; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(98)00245-4

Reference yield:

: 236743-51-4
1,2-epoxy-3-(tri-O-benzyl-α-L-fucopyranosyl)-propane

: 236743-96-7
(S)-1-(O-benzyl-N-tert-butoxycarbonyl-L-threonine)-2-(2-phenethoxy)-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Guidance literature:: Multi-step reaction with 4 steps

1: NaN₃, NH₄Cl / ethanol; H₂O / 1.5 h / Heating

2: 18 percent / NaOH, Bu₄NHSO₄ / H₂O / 120 h / Ambient temperature

3: 86 percent / PPh₃, H₂O / tetrahydrofuran / 30 h / Ambient temperature

4: 84 percent / EDC, HOBT, NMM / dimethylformamide / 21 h / -20 - 20 °C

With 4-methyl-morpholine; sodium hydroxide; sodium azide; water; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(98)00245-4