2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

Base Information

Chemical Name:2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine
CAS No.:552856-38-9
Molecular Formula:C₂₀H₂₄N₂O₁₀S₂
Molecular Weight:516.55
Hs Code.:

Synonyms:2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

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Chemical Property of 2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

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Technology Process of 2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

There total 11 articles about 2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine 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: 91.0%

: 293751-07-2
1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine

: 552856-38-9
2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;
DOI:10.1081/NCN-120022818

Reference yield:

: 293751-04-9
1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine

: 552856-38-9
2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / NH₃ / methanol

2: 93 percent / pyridine

3: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile

With pyridine; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; acetonitrile;
DOI:10.1081/NCN-120022818

Reference yield:

: 63593-03-3
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

: 552856-38-9
2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 258 mg / aq. H₂SO₄ / acetic acid / 2 h / 20 °C

2.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1.5 h / Heating

2.2: 91 percent / trimethylsilyl triflate / acetonitrile / 3.5 h / 0 - 80 °C

3.1: 84 percent / NH₃ / methanol / 20 °C

4.1: 93 percent / pyridine / 3 h / 0 - 15 °C

5.1: 91 percent / DBU / acetonitrile / 2 h

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; acetic acid; acetonitrile;
DOI:10.1039/b208864a