2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

Base Information

Chemical Name:2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester
CAS No.:119753-86-5
Molecular Formula:C₂₁H₂₄N₂O₁₀S
Molecular Weight:496.495
Hs Code.:

2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

Synonyms:2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

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Chemical Property of 2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

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Technology Process of 2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

There total 6 articles about 2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl 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: 71.0%

: 119754-04-0
2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(toluene-4-sulfonyl)-5-trityloxymethyl-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

: 119753-86-5
2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(01)90111-5

Reference yield:

: 96253-10-0
1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione

: 119753-86-5
2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) sodium methoxide / 1.) MeOH, 0 deg C, 30 min; 2.) MeOH, reflux, 20 h

2: 99 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h

3: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H₂O, 40 deg C, 2 h

4: 1.) NaH (80percent in mineral oil) / 1.) THF, 20 min; 2.) THF, 0 deg C, 48 h

5: 71 percent / 2percent trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; sodium methylate; sodium hydride; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0040-4020(01)90111-5

Reference yield:

: 119753-89-8
1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil

: 119753-86-5
2-[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-yl]-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h

2: 72 percent / methylsulfonyl chloride, pyridine / 1.) 0 deg C, 2.) H₂O, 40 deg C, 2 h

3: 1.) NaH (80percent in mineral oil) / 1.) THF, 20 min; 2.) THF, 0 deg C, 48 h

4: 71 percent / 2percent trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; sodium hydride; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0040-4020(01)90111-5