(2S,3S)-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

Base Information

• Chemical Name: (2S,3S)-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
• CAS No.: 473709-90-9
• Molecular Formula: C₄₉H₇₁N₃O₉Si₂
• Molecular Weight: 902.288

Synonyms:

Chemical Property of (2S,3S)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2S,3S)-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

There total 1 articles about (2S,3S)-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 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: 31.0%

tert-butyl 2-(dibenzylamino)ethanoate (94226-56-9) + 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde (137233-53-5) → 3-{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 + (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,3S)-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 (473709-90-9)

Guidance literature:

tert-butyl 2-(dibenzylamino)ethanoate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde; In tetrahydrofuran; at -78 - -35 ℃; for 17h;

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

Reference yield:

(2S,3S)-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 (473709-90-9) → (2S,3S)-2-Amino-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}-3-hydroxy-propionic acid tert-butyl ester (473709-92-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

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

Reference yield:

(2S,3S)-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 (473709-90-9) → (2S,3S)-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}-3-hydroxy-2-[3-(4-nitro-phenyl)-ureido]-propionic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd/C / methanol

2: tetrahydrofuran / 24 h / 20 °C

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

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

upstream raw materials:

tert-butyl 2-(dibenzylamino)ethanoate

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

Downstream raw materials:

(2S,3S)-2-Amino-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}-3-hydroxy-propionic acid tert-butyl ester

2-[3-(2-benzyloxycarbonylamino-3-hydroxy-butyrylamino)-propylamino]-3-{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}-3-hydroxy-propionic acid tert-butyl ester

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