1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

Base Information

Chemical Name:1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil
CAS No.:1275611-05-6
Molecular Formula:C₂₁H₂₆N₂O₁₂S₂
Molecular Weight:562.576
Hs Code.:

Synonyms:1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

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Chemical Property of 1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

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Technology Process of 1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

There total 1 articles about 1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil 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: 85.0%

: 66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6
uracil

: 410076-93-6
3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose

: 1275611-05-6
1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

Guidance literature:: uracil; 3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; Reflux; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 28h; Reflux; Inert atmosphere;

Reference yield: 97.0%

: 1275611-05-6
1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

: 1275611-06-7
1-[3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

Guidance literature:: With hydrogenchloride; In methanol; at 20 ℃; for 24h; Product distribution / selectivity;

Reference yield:

: 1275611-05-6
1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

: 1275611-14-7
(1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 10 steps

1: hydrogenchloride / methanol / 24 h / 20 °C

2: pyridine / 4 h / 20 °C / Inert atmosphere

3: sodium hydroxide; water / 1,4-dioxane / 4 h / 20 °C

4: N,N-dimethyl-formamide / 20 h / 90 °C / Inert atmosphere

5: ammonia / methanol / 14 h / 20 °C

6: formic acid / 20 wt% Pd(OH)2/C / water; tetrahydrofuran; methanol / 24 h / Reflux

7: pyridine / 14 h / 60 °C

8: iodine; ammonium cerium (IV) nitrate; acetic acid / 0.83 h / 80 °C

9: ammonia / methanol / 12 h / 20 °C / Sealed tube

10: pyridine / 16 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; formic acid; ammonium cerium (IV) nitrate; ammonia; water; iodine; acetic acid; sodium hydroxide; 20 wt% Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;