(3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

Base Information

Chemical Name:(3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine
CAS No.:1370411-72-5
Molecular Formula:C₂₈H₃₀N₂O₇
Molecular Weight:506.555
Hs Code.:

Synonyms:(3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

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Chemical Property of (3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

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Technology Process of (3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

There total 2 articles about (3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine 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: 73.0%

: 1370411-71-4
(2S,3R,3aR,6R,6aR)-3a,6-bis(benzyloxy)-2-(acetyloxy)-hexahydro-2H-cyclopenta[b]furan-3-yl acetate

: 65-71-4,28806-14-6,691841-57-3
thymin

: 1370411-72-5
(3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

Guidance literature:: (2S,3R,3aR,6R,6aR)-3a,6-bis(benzyloxy)-2-(acetyloxy)-hexahydro-2H-cyclopenta[b]furan-3-yl acetate; thymin; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 80 ℃; for 1h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 50 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo300554w

Reference yield:

: C₂₁H₂₄O₅

: 1370411-72-5
(3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 80 °C / Inert atmosphere

2.2: 16 h / 0 - 50 °C / Inert atmosphere

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile;
DOI:10.1021/jo300554w

Reference yield: 91.0%

: 1370411-72-5
(3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

: 1370411-74-7
(3'S,5'R)-1-(2'-hydroxy-3',5'-O-dibenzyl-3',5'-ethano-β-dribofuranosyl)thymidine

Guidance literature:: (3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine; With sodium methylate; In methanol; at 20 ℃; for 4h; Inert atmosphere;

With hydrogenchloride; In methanol; water;
DOI:10.1021/jo300554w