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

Base Information

• Chemical Name: (1S,3R,4S,7R)-7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 284497-21-8
• Molecular Formula: C₁₁H₁₄N₂O₆
• Molecular Weight: 270.242

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

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

Chemical Property:

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

There total 1 articles about (1S,3R,4S,7R)-7-hydroxy-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: 80.0%

(1S,3R,4S,7R)-7-benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (245366-57-8) → (1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (245366-58-9) + (1S,3R,4S,7R)-7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (284497-21-8)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 2h; Heating;

DOI:10.1021/jo000232g

Reference yield: 98.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1S,3R,4S,7R)-7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (284497-21-8) → (1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (245366-58-9)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/ja0168763

Reference yield:

(1S,3R,4S,7R)-7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (284497-21-8) → (1S,3R,4S,7R)-3-(4-N-benzoyl-5-methylcytosin-1-yl)-1-[[(4,4'-dimethoxytrityl)oxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 4 h

2.1: 18.7 g / pyridine

3.1: 97 percent / POCl₃; DIPEA / acetonitrile / 2 h / 20 °C

4.1: aq. ammonia / acetonitrile / 20 °C

4.2: pyridine

4.3: 81 percent / aq. NaOH / methanol / 1 h

With pyridine; ammonium hydroxide; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In acetonitrile;

DOI:10.1016/j.tet.2006.04.016

upstream raw materials:

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

Downstream raw materials:

(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

1-[3-O-acetyl-5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-α-L-ribofuranosyl]thymine

1-[3-O-acetyl-5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-α-L-ribofuranosyl]-5-methyl-4-(1,2,4-triazol-1-yl)-2-oxypyrimidine

(1S,3R,4S,7R)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-[[(4,4'-dimethoxytrityl)oxy]methyl]-3-(4-N-benzoyl-5-methylcytosin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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