1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

Base Information

Chemical Name:1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil
CAS No.:851050-47-0
Molecular Formula:C₂₃H₂₆N₂O₁₂S₂
Molecular Weight:586.598
Hs Code.:

Synonyms:1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

Suppliers and Price of 1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of 1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of 1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

There total 17 articles about 1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil 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: 88.0%

: 851050-46-9
1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose

: 66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6
uracil

: 851050-47-0
1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

Guidance literature:: 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose; uracil; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 50 ℃; for 39h; Heating;
DOI:10.1016/j.bmc.2005.01.029

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 851050-47-0
1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 16 steps

1.1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 20 °C

2.1: aq. acetic acid / 22 h

3.1: sodium periodate / tetrahydrofuran; H₂O / 2 h / 0 °C

4.1: 30.39 g / NaOH / dioxane; H₂O / 42 h / 20 °C

5.1: 71 percent / imidazole / dimethylformamide / 20 h / 35 °C

6.1: 76 percent / H₂ / Pd/C / ethanol / 18 h / 20 °C

7.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 21 h / 20 °C

8.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

8.2: 90 percent / tetrahydrofuran; cyclohexane / 1.25 h

9.1: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

10.1: pyridine; DMAP / 67 h / 20 °C

11.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 16 h / 20 °C

12.1: 3.38 g / aq. acetic acid / 23 h / 20 °C

13.1: pyridine / 20 h / 20 °C

14.1: aq. trifluoroacetic acid / 2 h / 0 °C

15.1: 4.50 g / pyridine / 20 h / 20 °C

16.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / Heating

16.2: 88 percent / trimethylsilyl triflate / acetonitrile / 39 h / 50 °C / Heating

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium periodate; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmc.2005.01.029

Reference yield:

: 851050-35-6
3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose

: 851050-47-0
1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 11 steps

1.1: 76 percent / H₂ / Pd/C / ethanol / 18 h / 20 °C

2.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 21 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

3.2: 90 percent / tetrahydrofuran; cyclohexane / 1.25 h

4.1: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

5.1: pyridine; DMAP / 67 h / 20 °C

6.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 16 h / 20 °C

7.1: 3.38 g / aq. acetic acid / 23 h / 20 °C

8.1: pyridine / 20 h / 20 °C

9.1: aq. trifluoroacetic acid / 2 h / 0 °C

10.1: 4.50 g / pyridine / 20 h / 20 °C

11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / Heating

11.2: 88 percent / trimethylsilyl triflate / acetonitrile / 39 h / 50 °C / Heating

With pyridine; dmap; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; cyclohexane; acetonitrile;
DOI:10.1016/j.bmc.2005.01.029