(1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 851050-48-1
• Molecular Formula: C₂₀H₂₀N₂O₈S
• Molecular Weight: 448.453
• Mol file: 851050-48-1.mol

Synonyms:(1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

There total 18 articles about (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 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: 94.0%

1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil (851050-47-0) → (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (851050-48-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2005.01.029

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (851050-48-1)

Guidance literature:

Multi-step reaction with 17 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

17.1: 94 percent / NaOH / dioxane; H₂O / 3 h / 20 °C

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:

3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose (851050-35-6) → (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (851050-48-1)

Guidance literature:

Multi-step reaction with 12 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

12.1: 94 percent / NaOH / dioxane; H₂O / 3 h / 20 °C

With pyridine; dmap; sodium hydroxide; 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; acetonitrile;

DOI:10.1016/j.bmc.2005.01.029

upstream raw materials:

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

3-C-ethynyl-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranose

3-O-benzyl-3-C-ethynyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranos-3-ulose

Downstream raw materials:

Benzoic acid (1R,3R,4R,7S)-7-benzyloxy-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-ethynyl-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

(1S,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(hydroxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane