(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

Base Information

• Chemical Name: (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde
• CAS No.: 172280-71-6
• Molecular Formula: C₃₈H₄₆N₂O₈Si
• Molecular Weight: 686.877
• Mol file: 172280-71-6.mol

Synonyms:(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

Chemical Property of (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

There total 2 articles about (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde 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:

3'-O-(tert-butyldimethylsilyl)-4'-(hydroxymethyl)-thymidine (139887-99-3) → (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde (172280-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalylchloride, triethylamine / dimethylsulfoxide

2: triethylamine / dimethylsulfoxide

With Chloro-oxo-acetic acid; triethylamine; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)78243-8

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) + (2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde (139888-01-0) → (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde (172280-71-6)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; Yield given;

DOI:10.1016/S0040-4039(00)78243-8

Reference yield: 65.0%

(hex-5-en-1-yl)triphenylphosphonium bromide (102112-92-5) + (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde (172280-71-6) → 1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-((E)-hepta-1,6-dienyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (172280-72-7)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)78243-8

upstream raw materials:

4,4'-dimethoxytrityl chloride

(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

3'-O-(tert-butyldimethylsilyl)-4'-(hydroxymethyl)-thymidine

Downstream raw materials:

1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-((E)-hepta-1,6-dienyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-((E)-7-hydroxy-hept-1-enyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

N-{(E)-7-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-hept-6-enyl}-2,2,2-trifluoro-acetamide

Methanesulfonic acid (E)-7-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-hept-6-enyl ester