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

Base Information

Chemical Name:[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-ylamino]-acetic acid methyl ester
CAS No.:119753-85-4
Molecular Formula:C₁₉H₂₃N₃O₈S
Molecular Weight:453.473
Hs Code.:

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

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

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

There total 6 articles about [(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-ylamino]-acetic acid methyl 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: 77.0%

: 119754-01-7
[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(toluene-4-sulfonyl)-5-trityloxymethyl-tetrahydro-furan-3-ylamino]-acetic acid methyl ester

: 119753-85-4
[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-ylamino]-acetic acid methyl ester

Guidance literature:: With acetic acid; for 0.166667h; Heating;
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

: 119753-85-4
[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-ylamino]-acetic acid methyl 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: 59 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / dimethylsulfoxide / Ambient temperature

5: 77 percent / 80percent aq. acetic acid / 0.17 h / Heating

With pyridine; sodium methylate; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide;
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

: 119753-85-4
[(2R,3S,4R,5R)-2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-ylamino]-acetic acid methyl 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: 59 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / dimethylsulfoxide / Ambient temperature

4: 77 percent / 80percent aq. acetic acid / 0.17 h / Heating

With pyridine; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4020(01)90111-5