(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester
CAS No.:154397-07-6
Molecular Formula:C₃₅H₄₄N₂O₁₇
Molecular Weight:764.738
Hs Code.:

(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Chemical Property of (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Technology Process of (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 15 articles about (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl 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:

: 51008-88-9
1,2,3,4-tetra-O-acetyl-D-mannopyranoside

: 154397-07-6
(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: RuCl₃*3H₂O, NaIO₄ / CCl₄; H₂O; acetonitrile

2: NaHCO₃ / dimethylformamide

3: 94 percent / 2-aminoethanol / ethyl acetate; dimethylsulfoxide

4: 92 percent / Na₂CO₃ / CH₂Cl₂

5: 85 percent / TMSOTf, molecular sieves / CH₂Cl₂ / 1.) -25 deg C, 16 h, 2.) -5 deg C, 6 h

6: H₂ / 10percent Pd/C / methanol

7: NaHCO₃ / dimethylformamide

With ruthenium trichloride; sodium periodate; molecular sieve; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; sodium carbonate; ethanolamine; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00081a004

Reference yield:

: 18968-50-8,29587-02-8,32166-85-1,36215-54-0,43138-65-4,65725-74-8,67816-77-7
1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol

: 154397-07-6
(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

2: Et₃N, DMAP / CH₂Cl₂

3: 80percent AcOH / 2 h / 90 °C

4: Et₃N / benzene

5: 80 percent / TMSOTf / CCl₄ / 6 h / Heating

6: 85 percent / NIS, TfOH / CH₂Cl₂ / -20 - 0 °C

7: NaOMe / methanol

8: 85 percent / TMSOTf, molecular sieves / CH₂Cl₂ / 1.) -25 deg C, 16 h, 2.) -5 deg C, 6 h

9: H₂ / 10percent Pd/C / methanol

10: NaHCO₃ / dimethylformamide

With dmap; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydrogencarbonate; acetic acid; triethylamine; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00081a004

Reference yield:

: 136399-55-8
2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

: 154397-07-6
(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(S)-1-[(2R,3R,4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-methoxy-tetrahydro-furan-2-yl]-2-hydroxy-ethoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaOMe / methanol

2: 85 percent / TMSOTf, molecular sieves / CH₂Cl₂ / 1.) -25 deg C, 16 h, 2.) -5 deg C, 6 h

3: H₂ / 10percent Pd/C / methanol

4: NaHCO₃ / dimethylformamide

With molecular sieve; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00081a004