1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

Base Information

Chemical Name:1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine
CAS No.:601512-85-0
Molecular Formula:C₂₀H₂₅N₅O₁₀S₂
Molecular Weight:559.578
Hs Code.:

Synonyms:1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

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Chemical Property of 1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

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Technology Process of 1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

There total 8 articles about 1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-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: 65.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 601512-84-9
1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-erythro-pentofuranosyl]thymine

: 601512-85-0
1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

Guidance literature:: trifluoromethylsulfonic anhydride; 1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-erythro-pentofuranosyl]thymine; With pyridine; dmap; In dichloromethane; at 0 ℃;

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1016/S0960-894X(03)00441-4

Reference yield:

: 601512-84-9
1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-erythro-pentofuranosyl]thymine

: 601512-85-0
1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

Guidance literature:: 1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-erythro-pentofuranosyl]thymine; With pyridine; dmap; trifluoromethanesulfonic acid anhydride; In dichloromethane; at -78 - 0 ℃; for 7h;

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1002/ejoc.200500023

Reference yield:

: 601512-83-8
2,2'-anhydro-1-[3-O-benzyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-erythro-pentofuranosyl]thymine

: 601512-85-0
1-[2-C-azido-3-O-benzyl-2-deoxy-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α-L-threo-pentofuranosyl]thymine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / aq. H₂SO₄ / acetone / 14 h / Heating

2.1: trifluoromethanesulfonic anhydride; DMAP; pyridine / CH₂Cl₂ / 7 h / -78 - 0 °C

2.2: 3.5 g / NaN₃ / dimethylformamide / 18 h / 20 °C

With pyridine; dmap; sulfuric acid; trifluoromethanesulfonic acid anhydride; In dichloromethane; acetone;
DOI:10.1002/ejoc.200500023