(2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol

Base Information

• Chemical Name: (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol
• CAS No.: 161452-72-8
• Molecular Formula: C₂₃H₂₅N₃O₄
• Molecular Weight: 407.469
• Mol file: 161452-72-8.mol

Synonyms:(2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol

Chemical Property of (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol

There total 15 articles about (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol 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: 97.0%

(2R)-1,4-anhydro-3,5-di-O-benzyl-2-deoxy-2-C-(uracil-1-yl)-D-arabitol (161452-71-7) → (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol (161452-72-8)

Guidance literature:

With dmap; ammonium hydroxide; Triphenylsilyl chloride; triethylamine; In acetonitrile; Ambient temperature; 1.) 3.5 h; 2.) 1.5 h;

DOI:10.1016/S0040-4020(01)81749-X

Reference yield:

1,2-isopropylidene-α-D-ribofuranose (37077-81-9) → (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol (161452-72-8)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / dimethylformamide / 13.5 h / Ambient temperature

2: 75 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et₃SiH / CH₂Cl₂ / 18.5 h / Ambient temperature

3: 97 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: 90 percent / LiN₃ / dimethylformamide / 6 h / 100 °C

5: 95 percent / H₂ / Lindlar catalyst / methanol; ethyl acetate / 6 h / Ambient temperature

6: 96 percent / benzene; dimethylformamide / 1.) -18 deg C, 1 h; 2.) RT, 1 h

7: 54 percent / 2.8percent NH₄OH / acetone / 10 h / 75 °C / glass sealed tube

8: 97 percent / 1.) Et₃N, TPSCl, DMAP; 2.) conc. NH₄OH / acetonitrile / Ambient temperature; 1.) 3.5 h; 2.) 1.5 h

With triethylsilane; dmap; ammonium hydroxide; lithium azide; Triphenylsilyl chloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; triethylamine; Lindlar's catalyst; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)81749-X

Reference yield:

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose (55735-86-9) → (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(cytosin-1-yl)-2-deoxy-D-arabitol (161452-72-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et₃SiH / CH₂Cl₂ / 18.5 h / Ambient temperature

2: 97 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

3: 90 percent / LiN₃ / dimethylformamide / 6 h / 100 °C

4: 95 percent / H₂ / Lindlar catalyst / methanol; ethyl acetate / 6 h / Ambient temperature

5: 96 percent / benzene; dimethylformamide / 1.) -18 deg C, 1 h; 2.) RT, 1 h

6: 54 percent / 2.8percent NH₄OH / acetone / 10 h / 75 °C / glass sealed tube

7: 97 percent / 1.) Et₃N, TPSCl, DMAP; 2.) conc. NH₄OH / acetonitrile / Ambient temperature; 1.) 3.5 h; 2.) 1.5 h

With triethylsilane; dmap; ammonium hydroxide; lithium azide; Triphenylsilyl chloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; triethylamine; Lindlar's catalyst; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)81749-X

upstream raw materials:

(2R)-1,4-anhydro-3,5-di-O-benzyl-2-deoxy-2-C-(uracil-1-yl)-D-arabitol

1,2-isopropylidene-α-D-ribofuranose

(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-pentanetriol

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose