(2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

Base Information

Chemical Name:(2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde
CAS No.:583843-93-0
Molecular Formula:C₂₈H₃₂N₂O₈
Molecular Weight:524.571
Hs Code.:

(2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

Synonyms:(2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

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Chemical Property of (2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

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Technology Process of (2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

There total 7 articles about (2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-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:

: 583843-92-9
3'-O-benzyl-3-N-(benzyloxymethyl)-3'-C-((methoxymethoxy)methyl)thymidine

: 583843-93-0
(2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tetlet.2004.04.082

Reference yield:

: 131607-35-7
3'-deoxy-3'-C-methylidene-5'-O-(triphenylmethyl)thymidine

: 583843-93-0
(2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: 65 percent / N-methylmorpholine N-oxide; pyridine; H₂O / osmium tetroxide / 2-methyl-propan-2-ol / 8 h / 75 °C

2.1: 89 percent / DBU / dimethylformamide / 5 h / 20 °C

3.1: dibutyltin dimethoxide / dioxane / 5 h / Heating

3.2: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 2 h / 20 °C

4.1: 84 percent / NaH; n-Bu₄NI / dimethylformamide / 6 h / 20 °C

5.1: 90 percent / (+)-10-camphorsulfonic acid; MeOH / CH₂Cl₂ / 9 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With pyridine; methanol; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dibutyldimethoxytin; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; osmium(VIII) oxide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.06.040

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 583843-93-0
(2S,3R,5R)-3-Benzyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxymethoxymethyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 89 percent / DBU / dimethylformamide / 5 h / 20 °C

2.1: dibutyltin dimethoxide / dioxane / 5 h / Heating

2.2: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 2 h / 20 °C

3.1: 84 percent / NaH; n-Bu₄NI / dimethylformamide / 6 h / 20 °C

4.1: 90 percent / (+)-10-camphorsulfonic acid; MeOH / CH₂Cl₂ / 9 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With methanol; tetra-(n-butyl)ammonium iodide; sodium hydride; dibutyldimethoxytin; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 5.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.06.040