(S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

Base Information

Chemical Name:(S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester
CAS No.:155023-04-4
Molecular Formula:C₄₆H₄₉N₅O₁₄
Molecular Weight:895.92
Hs Code.:

(S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

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Chemical Property of (S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

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Technology Process of (S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

There total 9 articles about (S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl 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: 54.0%

: 52471-73-5
(2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoic acid

: (S)-Amino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester; compound with trifluoro-acetic acid

: 155023-04-4
(S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

Guidance literature:: With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1039/c39940000111

Reference yield:

: 52471-72-4
Carbamic acid (2S,3S,4R)-2,3-bis-benzyloxy-4-benzyloxycarbonylamino-5-hydroxy-pentyl ester

: 155023-04-4
(S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: CrO₃, aq. H₂SO₄ / acetone / 0 °C

2: 54 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / Ambient temperature

With chromium(VI) oxide; diethyl cyanophosphonate; sulfuric acid; triethylamine; In N,N-dimethyl-formamide; acetone;
DOI:10.1039/c39940000111

Reference yield:

: (R)-4-((1S,2S)-1,2-Bis-benzyloxy-3-hydroxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 155023-04-4
(S)-((2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoylamino)-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

2: NH₃ / methanol; CH₂Cl₂

3: TsOH / methanol

4: CrO₃, aq. H₂SO₄ / acetone / 0 °C

5: 54 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / Ambient temperature

With chromium(VI) oxide; diethyl cyanophosphonate; sulfuric acid; ammonia; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/c39940000111