1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
CAS No.:119753-83-2
Molecular Formula:C₂₁H₂₇N₃O₆S
Molecular Weight:449.528
Hs Code.:

Synonyms:1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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Chemical Property of 1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

There total 6 articles about 1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 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: 78.0%

: 119753-99-0
1-[(2R,3S,4R,5R)-3-Piperidin-1-yl-4-(toluene-4-sulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

: 119753-83-2
1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h;
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

: 119753-83-2
1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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: 98 percent / tetrahydrofuran / 5 h / Ambient temperature

5: 78 percent / 2percent trifluoroacetic acid / CH₂Cl₂ / 3 h / 0 °C

With pyridine; sodium methylate; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; 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

: 119753-83-2
1-[(2R,3S,4R,5R)-5-Hydroxymethyl-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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: 98 percent / tetrahydrofuran / 5 h / Ambient temperature

4: 78 percent / 2percent trifluoroacetic acid / CH₂Cl₂ / 3 h / 0 °C

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