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

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Chemical Name:(2S,3S)-3-Allyloxy-2-[(2S,3R)-4-benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyric acid ethyl ester
CAS No.:236744-34-6
Molecular Formula:C₅₈H₆₈N₂O₁₃
Molecular Weight:1001.18
Hs Code.:

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

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

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Chemical Property of (2S,3S)-3-Allyloxy-2-[(2S,3R)-4-benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyric acid ethyl ester

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Technology Process of (2S,3S)-3-Allyloxy-2-[(2S,3R)-4-benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyric acid ethyl ester

There total 6 articles about (2S,3S)-3-Allyloxy-2-[(2S,3R)-4-benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyric acid ethyl 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: 69.0%

: 215163-68-1
(2R,3S)-4-benzyloxy-3-hydroxy-2-monobenzylsuccinamidyl-butanoic acid

: (2S,3S)-3-Allyloxy-2-amino-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyric acid ethyl ester

: 236744-34-6
(2S,3S)-3-Allyloxy-2-[(2S,3R)-4-benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyric acid ethyl ester

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 - 20 ℃; for 11h;
DOI:10.1016/S0968-0896(98)00245-4

Reference yield:

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

: 236744-34-6
(2S,3S)-3-Allyloxy-2-[(2S,3R)-4-benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-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 / pyridine / 25 h / 4 °C

2: 88 percent / NaN₃ / dimethylformamide / 21 h / 50 °C

3: 85 percent / H₂ / Pd/C / ethyl acetate / 18 h / Ambient temperature

4: 88 percent / Pd₂(dba)3, bdpb / tetrahydrofuran / 8 h / 65 - 70 °C

5: TFA / CH₂Cl₂ / 3.5 h / 0 - 20 °C

6: 69 percent / EDC, HOBT, NMM / CH₂Cl₂ / 11 h / 0 - 20 °C

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

Reference yield:

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

: 236744-34-6
(2S,3S)-3-Allyloxy-2-[(2S,3R)-4-benzyloxy-2-(3-benzyloxycarbonyl-propionylamino)-3-hydroxy-butyrylamino]-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 4 steps

1: 85 percent / H₂ / Pd/C / ethyl acetate / 18 h / Ambient temperature

2: 88 percent / Pd₂(dba)3, bdpb / tetrahydrofuran / 8 h / 65 - 70 °C

3: TFA / CH₂Cl₂ / 3.5 h / 0 - 20 °C

4: 69 percent / EDC, HOBT, NMM / CH₂Cl₂ / 11 h / 0 - 20 °C

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