(S)-Benzyloxycarbonylamino-[(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

Base Information

Chemical Name:(S)-Benzyloxycarbonylamino-[(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
CAS No.:127559-13-1
Molecular Formula:C₁₉H₂₁N₃O₉
Molecular Weight:435.39
Hs Code.:

Synonyms:(S)-Benzyloxycarbonylamino-[(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

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Chemical Property of (S)-Benzyloxycarbonylamino-[(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

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Technology Process of (S)-Benzyloxycarbonylamino-[(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

There total 41 articles about (S)-Benzyloxycarbonylamino-[(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 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:

: 127257-34-5
methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate

: 127559-13-1
(S)-Benzyloxycarbonylamino-[(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

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;
DOI:10.1021/jo00299a017

Reference yield:

: 205513-89-9
(S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

: 127559-13-1
(S)-Benzyloxycarbonylamino-[(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

Guidance literature:: With hydrogenchloride; lithium hydroxide; 1.) THF;
DOI:10.3987/COM-97-S30

Reference yield:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 127559-13-1
(S)-Benzyloxycarbonylamino-[(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

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) t-BuLi; 2.) O₃; 3.) M₂S / 1.) THF, -78 deg C; 2.) CH₂Cl₂; 3.) CH₂Cl₂

2: 83 percent / pyridine / CH₂Cl₂

3: 86 percent / CsF / dimethylformamide

4: 65 percent / EtONa / ethanol

5: 64 percent / pyridine / CH₂Cl₂

6: 86 percent / NaN₃ / dimethylformamide

7: Dowex 50 WH⁽¹⁺⁾ / Heating

8: pyridine

9: 88 percent / AcOH, conc. H₂SO₄ / CH₂Cl₂

10: 84 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Heating

11: hydrogen / 20percent Pd(OH)2/C / methanol

12: 7percent aq. NaHCO₃ / dioxane

13: 1.) LiOH*H₂O; 2.) 0.1 N HCl / 1.) THF

With pyridine; hydrogenchloride; lithium hydroxide; sodium azide; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; Dowex 50 WH⁽¹⁺⁾; sulfuric acid; hydrogen; tert.-butyl lithium; sodium ethanolate; sodium hydrogencarbonate; ozone; acetic acid; cesium fluoride; palladium dihydroxide; In 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3987/COM-97-S30