(2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid

Base Information

• Chemical Name: (2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid
• CAS No.: 473710-95-1
• Molecular Formula: C₃₆H₄₇N₅O₁₂
• Molecular Weight: 741.795

Synonyms:

Chemical Property of (2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid

There total 7 articles about (2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic 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:

2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde (137233-53-5) → (2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid (473710-95-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 31 percent / tetrahydrofuran / 17 h / -78 - -35 °C

2.1: H₂ / 10 percent Pd/C / methanol

3.1: NaBH(OAc)3; AcOH / tetrahydrofuran / 20 °C

4.1: nBu₄NF / tetrahydrofuran

5.1: TFA / CH₂Cl₂

With tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(03)00671-1

Reference yield:

(2S,3R)-3-{(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-2-dibenzylamino-3-hydroxy-propionic acid tert-butyl ester (473709-91-0) → (2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid (473710-95-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10 percent Pd/C / methanol

2: NaBH(OAc)3; AcOH / tetrahydrofuran / 20 °C

3: nBu₄NF / tetrahydrofuran

4: TFA / CH₂Cl₂

With tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(03)00671-1

Reference yield:

(2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid tert-butyl ester (473710-93-9) → (2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid (473710-95-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(03)00671-1

upstream raw materials:

(2S,3R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propylamino]-3-{(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid tert-butyl ester

2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde

[(S)-3-Methyl-1-(3-oxo-propylcarbamoyl)-butyl]-carbamic acid benzyl ester

[(S)-1-(3,3-Diethoxy-propylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester

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