(1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane

Base Information

• Chemical Name: (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane
• CAS No.: 229469-49-2
• Molecular Formula: C₂₇H₂₇N₃O₇
• Molecular Weight: 505.527
• Mol file: 229469-49-2.mol

Synonyms:

Chemical Property of (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane

There total 17 articles about (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane 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:

methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside (164454-52-8) → (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane (229469-49-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) DCC, TFA, pyridine, 2.) oxalic acid / 1.) DMSO, Et₂O, room temperature, 5 h, 2.) MeOH, room temperature, 1 h

2: 91 percent / sodium t-pentoxide / diethyl ether; benzene / 1.) room temperature, 6 h, 2.) -10 deg C, 1 h

3: 88 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

4: pyridine / 15 h / Ambient temperature

5: 76 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

6: 1.) 9-BBN, 2.) sodium perborate tetrahydrate / 1.) room temperature, 1 h; 40 deg C, overnight, 2.) H₂O, EtOH, 50 deg C, 4 h

7: pyridine / Ambient temperature

8: TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

9: 90 percent / DCC, TFA, pyridine / dimethylsulfoxide / 1.) 10 deg C, 1 h, 2.) room temperature, 6 h

10: 94 percent / NaOH / H₂O; dioxane / 48 h / Ambient temperature

11: pyridine / 0.75 h / Ambient temperature

12: AcOH / H₂O / 2 h / Ambient temperature

13: NaH / tetrahydrofuran / 28 h / 55 °C

14: NaOH / H₂O / 24 h / Heating

15: 99 percent / DMAP / CH₂Cl₂ / 2 h / Ambient temperature

16: 1.) ammonium sulfate, HMDS, 2.) SnCl₄ / 1.) reflux, overnight, 2.) 1,2-dichloroethane, reflux, 2 h

With pyridine; dmap; sodium perborate; sodium hydroxide; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; oxalic acid; tin(IV) chloride; sodium tert-pentoxide; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; dichloromethane; water; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4020(99)00394-4

Reference yield:

methyl D-arabinofuranoside (56607-40-0) → (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane (229469-49-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 88 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h

2: 1.) DCC, TFA, pyridine, 2.) oxalic acid / 1.) DMSO, Et₂O, room temperature, 5 h, 2.) MeOH, room temperature, 1 h

3: 91 percent / sodium t-pentoxide / diethyl ether; benzene / 1.) room temperature, 6 h, 2.) -10 deg C, 1 h

4: 88 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

5: pyridine / 15 h / Ambient temperature

6: 76 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

7: 1.) 9-BBN, 2.) sodium perborate tetrahydrate / 1.) room temperature, 1 h; 40 deg C, overnight, 2.) H₂O, EtOH, 50 deg C, 4 h

8: pyridine / Ambient temperature

9: TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

10: 90 percent / DCC, TFA, pyridine / dimethylsulfoxide / 1.) 10 deg C, 1 h, 2.) room temperature, 6 h

11: 94 percent / NaOH / H₂O; dioxane / 48 h / Ambient temperature

12: pyridine / 0.75 h / Ambient temperature

13: AcOH / H₂O / 2 h / Ambient temperature

14: NaH / tetrahydrofuran / 28 h / 55 °C

15: NaOH / H₂O / 24 h / Heating

16: 99 percent / DMAP / CH₂Cl₂ / 2 h / Ambient temperature

17: 1.) ammonium sulfate, HMDS, 2.) SnCl₄ / 1.) reflux, overnight, 2.) 1,2-dichloroethane, reflux, 2 h

With pyridine; dmap; sodium perborate; sodium hydroxide; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; oxalic acid; tin(IV) chloride; sodium tert-pentoxide; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; dichloromethane; water; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4020(99)00394-4

Reference yield:

(2R,3S,5S)-2-Hydroxymethyl-5-methoxy-4-methylene-tetrahydro-furan-3-ol (229469-30-1) → (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(cytosin-1-yl)-2,6-dioxabicyclo<3.2.1>octane (229469-49-2)

Guidance literature:

Multi-step reaction with 13 steps

1: pyridine / 15 h / Ambient temperature

2: 76 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

3: 1.) 9-BBN, 2.) sodium perborate tetrahydrate / 1.) room temperature, 1 h; 40 deg C, overnight, 2.) H₂O, EtOH, 50 deg C, 4 h

4: pyridine / Ambient temperature

5: TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

6: 90 percent / DCC, TFA, pyridine / dimethylsulfoxide / 1.) 10 deg C, 1 h, 2.) room temperature, 6 h

7: 94 percent / NaOH / H₂O; dioxane / 48 h / Ambient temperature

8: pyridine / 0.75 h / Ambient temperature

9: AcOH / H₂O / 2 h / Ambient temperature

10: NaH / tetrahydrofuran / 28 h / 55 °C

11: NaOH / H₂O / 24 h / Heating

12: 99 percent / DMAP / CH₂Cl₂ / 2 h / Ambient temperature

13: 1.) ammonium sulfate, HMDS, 2.) SnCl₄ / 1.) reflux, overnight, 2.) 1,2-dichloroethane, reflux, 2 h

With pyridine; dmap; sodium perborate; sodium hydroxide; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; tin(IV) chloride; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(99)00394-4

upstream raw materials:

4-N-benzoylcytosine

(1R,3S,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-methoxy-2,6-dioxabicyclo<3.2.1>octane

methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside

methyl D-arabinofuranoside