1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine

Base Information

• Chemical Name: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine
• CAS No.: 197452-38-3
• Molecular Formula: C₂₃H₁₈F₂IN₃O₆
• Molecular Weight: 597.314
• Mol file: 197452-38-3.mol

Synonyms:

Chemical Property of 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine

There total 6 articles about 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine 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:

benzoyl chloride (98-88-4) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine (197452-38-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 36 h / Ambient temperature

2: 33 percent / Li(t-BuO)3AlH / tetrahydrofuran / 0.67 h / -50 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) HMDS, (NH₄)2SO₄, 2.) TMSOTf / 1.) 125 deg C, 4 h, 2.) dichloroethane, from 90 to 100 deg C, 10 h

With 2,6-dimethylpyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm970275y

Reference yield:

(4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one (166275-25-8) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine (197452-38-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 36 h / Ambient temperature

2: 33 percent / Li(t-BuO)3AlH / tetrahydrofuran / 0.67 h / -50 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) HMDS, (NH₄)2SO₄, 2.) TMSOTf / 1.) 125 deg C, 4 h, 2.) dichloroethane, from 90 to 100 deg C, 10 h

With 2,6-dimethylpyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm970275y

Reference yield:

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentofuranose (143157-25-9,143157-22-6) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine (197452-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) HMDS, (NH₄)2SO₄, 2.) TMSOTf / 1.) 125 deg C, 4 h, 2.) dichloroethane, from 90 to 100 deg C, 10 h

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1021/jm970275y

upstream raw materials:

5-iodocytosine

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-(methylsulfonyl)-L-erythro-pentofuranose

benzoyl chloride

(4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one

Refernces