[(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

Base Information

Chemical Name:[(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
CAS No.:119754-01-7
Molecular Formula:C₃₈H₃₇N₃O₈S
Molecular Weight:695.793
Hs Code.:

[(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

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Chemical Property of [(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

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Technology Process of [(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

There total 5 articles about [(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 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: 59.0%

: 5680-79-5,883886-67-7
glycine ethyl ester hydrochloride

: 119753-91-2
1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil

: 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

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; 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

: 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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; sodium methylate; 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

: 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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; 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