(1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane

Base Information

• Chemical Name: (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane
• CAS No.: 322390-95-4
• Molecular Formula: C₂₇H₂₈N₂O₇
• Molecular Weight: 492.529

Synonyms:(1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane

Chemical Property of (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane

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Technology Process of (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane

There total 13 articles about (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane 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: 52.0%

thymin (65-71-4,28806-14-6,691841-57-3) + (1R,3R,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-methoxy-2,5,8-trioxatricyclo[5.3.1.04,11]undecane (322390-93-2) → (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.04,11]undecane (322390-95-4)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 - 60 ℃; for 48h;

DOI:10.1039/b006082h

Reference yield: 52.0%

thymin (65-71-4,28806-14-6,691841-57-3) + (1R,3S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-methoxy-2,5,8-trioxatricyclo[5.3.1.04,11]undecane (322390-94-3) → (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.04,11]undecane (322390-95-4)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 - 60 ℃; for 48h;

DOI:10.1039/b006082h

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → (1R,3R/S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-(thymin-1-yl)-2,5,8-trioxatricyclo[5.3.1.04,11]undecane (322390-95-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tetrahydrofuran; diethyl ether / 42 h

2.1: 14.9 g / aq. AcOH / 16 h

3.1: 94 percent / pyridine / 50 h / 20 °C

4.1: NaH / dimethylformamide / 1 h / 50 °C

4.2: 70 percent / dimethylformamide / 16 h / 20 °C

5.1: 76 percent / aq. HCl / 16 h / 20 °C

6.1: pyridine / 0.5 h / 20 °C

7.1: 1.152 g / aq. OsO₄; N-methylmorpholine N-oxide; pyridine / 2-methyl-propan-2-ol / 48 h / 80 °C

8.1: 490 mg / NaH / dimethylformamide / 96 h / 20 °C

9.1: 52 percent / N,O-bis(trimethylsilyl)acetamide; TMS triflate / acetonitrile / 48 h / 20 - 60 °C

With pyridine; hydrogenchloride; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Grignard reaction;

DOI:10.1039/b006082h

upstream raw materials:

thymin

(1R,3R,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-methoxy-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane

(1R,3S,4S,7R,10R,11R)-10,11-Dibenzyloxy-3-methoxy-2,5,8-trioxatricyclo[5.3.1.0^4,11]undecane

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

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