(1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:774598-96-8
Molecular Formula:C₂₁H₂₅N₅O₆
Molecular Weight:443.459
Hs Code.:

Synonyms:(1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

There total 5 articles about (1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 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: 63.0%

: 774598-95-7
1-(2-O-acetyl-3-C-(3-azidopropyl)-3-O-benzyl-5-O-mesyl-4-C-mesyloxymethyl-β-D-erythro-pentofuranosyl)thymine

: 774598-96-8
(1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With potassium hydroxide; In 1,4-dioxane; for 41h; Heating;
DOI:10.1021/jo049159a

Reference yield:

: 774598-93-5
3-C-(3-azidopropyl)-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

: 774598-96-8
(1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 4.5 h / 20 °C

2: aq. TFA / 3.5 h / 20 °C

3: 1.98 g / pyridine; DMAP / 15 h / 20 °C

4: 75 percent / N,O-bistrimethyl acetamide; trimethylsilyl triflate / acetonitrile / Heating

5: 63 percent / aq. KOH / dioxane / 41 h / Heating

With pyridine; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; N,O-bistrimethyl acetamide; trifluoroacetic acid; In 1,4-dioxane; acetonitrile;
DOI:10.1021/jo049159a

Reference yield:

: Methanesulfonic acid (3S,4R)-3-(3-azido-propyl)-3-benzyloxy-4,5-dihydroxy-2-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester

: 774598-96-8
(1S,3R,4R,7S)-7-(3-azidopropyl)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

1: 1.98 g / pyridine; DMAP / 15 h / 20 °C

2: 75 percent / N,O-bistrimethyl acetamide; trimethylsilyl triflate / acetonitrile / Heating

3: 63 percent / aq. KOH / dioxane / 41 h / Heating

With pyridine; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; N,O-bistrimethyl acetamide; In 1,4-dioxane; acetonitrile;
DOI:10.1021/jo049159a