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

Base Information

• Chemical Name: (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-7-(2-hydroxyethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 774598-77-5
• Molecular Formula: C₃₄H₃₆N₂O₉
• Molecular Weight: 616.668
• Mol file: 774598-77-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-7-(2-hydroxyethyl)-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:

(1R,3R,4R,7S)-7-allyl-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (774598-75-3) → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-7-(2-hydroxyethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (774598-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaIO₄; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

2: 813 mg / NaBH₄ / tetrahydrofuran; H₂O / 20 h

3: 83 percent / NH₄HCO₃ / Pd/C / methanol / 2.5 h / 70 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; ammonium bicarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; tert-butyl alcohol;

DOI:10.1021/jo049159a

Reference yield:

[(1R,3R,4R,7S)-7-Benzyloxy-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dioxa-bicyclo[2.2.1]hept-7-yl]-acetaldehyde → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-7-(2-hydroxyethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (774598-77-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 813 mg / NaBH₄ / tetrahydrofuran; H₂O / 20 h

2: 83 percent / NH₄HCO₃ / Pd/C / methanol / 2.5 h / 70 °C

With sodium tetrahydroborate; ammonium bicarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo049159a

Reference yield:

Acetic acid (3S,4R)-2-acetoxymethyl-3-allyl-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-ylmethyl ester → (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityl)oxymethyl-7-hydroxy-7-(2-hydroxyethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (774598-77-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 3.38 g / pyridine; DMAP / 12 h / 20 °C

2: 63 percent / N,O-(bistrimethyl)acetamide; trimethylsilyl triflate / acetonitrile / 3 h / Heating

3: 81 percent / NaOMe / methanol / 1 h / 20 °C

4: 70 percent / pyridine / 0 - 20 °C

5: 74 percent / pyridine / 42 h

6: 96 percent / NaH / dimethylformamide / 20 h / 20 °C

7: NaIO₄; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

8: 813 mg / NaBH₄ / tetrahydrofuran; H₂O / 20 h

9: 83 percent / NH₄HCO₃ / Pd/C / methanol / 2.5 h / 70 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; N,O-(bistrimethyl)acetamide; sodium methylate; sodium hydride; ammonium bicarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo049159a

upstream raw materials:

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

3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

(R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

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