(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester
CAS No.:154397-09-8
Molecular Formula:C₃₅H₄₃N₃O₁₇
Molecular Weight:777.736
Hs Code.:

(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Synonyms:(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Chemical Property of (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Technology Process of (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 18 articles about (2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-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

: 154397-09-8
(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 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

8: PDC, molecular sieves / dimethylformamide; acetic acid

9: N-hydroxysuccinimide*NH₃, DIPC / dimethylformamide

With ruthenium trichloride; sodium periodate; dipyridinium dichromate; molecular sieve; bis-2-propyl carbonate; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; sodium carbonate; ethanolamine; N-hydroxysuccinimide ammonium salt; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; water; acetic acid; 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

: 154397-09-8
(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 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

11: PDC, molecular sieves / dimethylformamide; acetic acid

12: N-hydroxysuccinimide*NH₃, DIPC / dimethylformamide

With dmap; N-iodo-succinimide; dipyridinium dichromate; molecular sieve; bis-2-propyl carbonate; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydrogencarbonate; acetic acid; N-hydroxysuccinimide ammonium salt; triethylamine; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; acetic acid; 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

: 154397-09-8
(2S,3S,4S,5S,6S)-3,4,5-Triacetoxy-6-{(R)-carbamoyl-[(2S,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]-methoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 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

5: PDC, molecular sieves / dimethylformamide; acetic acid

6: N-hydroxysuccinimide*NH₃, DIPC / dimethylformamide

With dipyridinium dichromate; molecular sieve; bis-2-propyl carbonate; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydrogencarbonate; N-hydroxysuccinimide ammonium salt; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo00081a004