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

Base Information

• Chemical Name: 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose
• CAS No.: 851050-46-9
• Molecular Formula: C₂₁H₂₆O₁₂S₂
• Molecular Weight: 534.562
• Mol file: 851050-46-9.mol

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

Chemical Property of 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose

There total 16 articles about 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose 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:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose (851050-46-9)

Guidance literature:

Multi-step reaction with 15 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

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium periodate; n-butyllithium; 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;

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

Guidance literature:

Multi-step reaction with 10 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

With pyridine; dmap; n-butyllithium; 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;

DOI:10.1016/j.bmc.2005.01.029

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose (851050-46-9)

Guidance literature:

Multi-step reaction with 13 steps

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

2.1: 30.39 g / NaOH / dioxane; H₂O / 42 h / 20 °C

3.1: 71 percent / imidazole / dimethylformamide / 20 h / 35 °C

4.1: 76 percent / H₂ / Pd/C / ethanol / 18 h / 20 °C

5.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 21 h / 20 °C

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

6.2: 90 percent / tetrahydrofuran; cyclohexane / 1.25 h

7.1: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

8.1: pyridine; DMAP / 67 h / 20 °C

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

10.1: 3.38 g / aq. acetic acid / 23 h / 20 °C

11.1: pyridine / 20 h / 20 °C

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

13.1: 4.50 g / pyridine / 20 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium periodate; n-butyllithium; 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;

DOI:10.1016/j.bmc.2005.01.029

upstream raw materials:

acetic anhydride

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

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

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

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