ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

Base Information

Chemical Name:ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate
CAS No.:236744-30-2
Molecular Formula:C₃₉H₄₃NO₁₂S
Molecular Weight:749.836
Hs Code.:

Synonyms:ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

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Chemical Property of ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

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Technology Process of ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

There total 1 articles about ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate 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: 88.0%

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: ethyl (2R,3S)-2,3-dihydroxy-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

: 236744-30-2
ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

Guidance literature:: In pyridine; at 4 ℃; for 25h;
DOI:10.1016/S0968-0896(98)00245-4

Reference yield: 88.0%

: 236744-30-2
ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

: 236744-31-3
ethyl (2R,3S)-2-azido-3-hydroxy-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 21h;
DOI:10.1016/S0968-0896(98)00245-4

Reference yield:

: 236744-30-2
ethyl (2R,3S)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-4-(tri-O-benzyl-α-L-fucopyranosyl)-butanoate

: (2S,3S)-2-[(2S,3R)-4-Benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-3-((E)-3-phenyl-allyloxy)-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / NaN₃ / dimethylformamide / 21 h / 50 °C

2: 85 percent / H₂ / Pd/C / ethyl acetate / 18 h / Ambient temperature

3: 88 percent / Pd₂(dba)3, bdpb / tetrahydrofuran / 8 h / 65 - 70 °C

4: TFA / CH₂Cl₂ / 3.5 h / 0 - 20 °C

5: 69 percent / EDC, HOBT, NMM / CH₂Cl₂ / 11 h / 0 - 20 °C

6: Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / Heating

With 4-methyl-morpholine; Grubbs catalyst first generation; sodium azide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(98)00245-4