(1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane

Base Information

• Chemical Name: (1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane
• CAS No.: 557099-55-5
• Molecular Formula: C₂₄H₂₈O₇
• Molecular Weight: 428.482

Synonyms:(1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane

Chemical Property of (1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane

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Technology Process of (1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane

There total 1 articles about (1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]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: 86.0%

(1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02.6]undec-10-ene (352422-83-4) → (1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.03,7]undecane (557099-55-5)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; tert-butyl alcohol; at 60 ℃; for 4h;

DOI:10.1039/b210439c

Reference yield: 76.0%

acetic anhydride (108-24-7) + (1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.03,7]undecane (557099-55-5) → (1R,3R,7R,8R,9S,10S,11R)-9,10-diacetyloxy-8,11-dibenzyloxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.03,7]undecane (557099-56-6)

Guidance literature:

With pyridine; at 20 ℃; for 16h;

DOI:10.1039/b210439c

Reference yield:

(1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.03,7]undecane (557099-55-5) → (1R,3R,4R,5R,6S,7S,8R)-4,6,7-triacetyloxy-5,8-dibenzyloxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane (557099-58-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / pyridine / 16 h / 20 °C

2: aq. AcOH / 16 h / 90 °C

3: 200 mg / pyridine / 16 h

4: 65 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 16 h / 50 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; acetic acid; In acetonitrile;

DOI:10.1039/b210439c

upstream raw materials:

(1R,2R,6R,8R,9R)-1,9-Bis(benzyloxy)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.0^2.6]undec-10-ene

Downstream raw materials:

(1R,3R,7R,8R,9S,10S,11R)-9,10-diacetyloxy-8,11-dibenzyloxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane

(3RS,1R,4R,5R,6S,7S,8R)-3,4,6,7-tetraacetyloxy-5,8-dibenzyloxy-2-oxabicyclo[3.3.0]octane

(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

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