(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Base Information

• Chemical Name: (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene
• CAS No.: 352422-94-7
• Molecular Formula: C₃₃H₂₅F₅N₂O₇S
• Molecular Weight: 688.629
• Mol file: 352422-94-7.mol

Synonyms:(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Chemical Property of (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

There total 17 articles about (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene 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: 20.0%

pentafluorophenoxythiocarbonyl chloride (135192-53-9) + (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (352422-92-5) → (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (352422-94-7)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/b101364p

Reference yield:

benzyl bromide (100-39-0) → (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (352422-94-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

1.2: 27 / 16 h / 20 °C

2.1: periodic acid / ethyl acetate / 1 h / 20 °C

3.1: tetrahydrofuran / 48 h / 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride / dichloromethane / 1 h / 40 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

5.2: 27 / 16 h / 20 °C

6.1: water; acetic acid / 16 h / 90 °C

7.1: pyridine / 16 h / 20 °C

8.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.25 h / Heating

8.2: TMS triflate / 7 / 16 h / 50 °C

9.1: sodium methylate / methanol / 16 h / 20 °C

10.1: dmap / dichloromethane / 16 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; sodium methylate; sodium hydride; periodic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 3.1: Grignard addition;

DOI:10.1039/b101364p

Reference yield:

(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]-dioxol-6-ol (51996-47-5) → (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-pentafluorophenoxythiocarbonyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (352422-94-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

1.2: 27 / 16 h / 20 °C

2.1: periodic acid / ethyl acetate / 1 h / 20 °C

3.1: tetrahydrofuran / 48 h / 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride / dichloromethane / 1 h / 40 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

5.2: 27 / 16 h / 20 °C

6.1: water; acetic acid / 16 h / 90 °C

7.1: pyridine / 16 h / 20 °C

8.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.25 h / Heating

8.2: TMS triflate / 7 / 16 h / 50 °C

9.1: sodium methylate / methanol / 16 h / 20 °C

10.1: dmap / dichloromethane / 16 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; sodium methylate; sodium hydride; periodic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 3.1: Grignard addition;

DOI:10.1039/b101364p

upstream raw materials:

pentafluorophenoxythiocarbonyl chloride

(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

(1R,3R,4R,5R,8R)-4-Acetoxy-5,8-bis(benzyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

benzyl bromide

Downstream raw materials:

(1R,3R,5R,8R)-5,8-Bis(benzyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane