(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

Base Information

• Chemical Name: (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
• CAS No.: 557099-56-6
• Molecular Formula: C₂₈H₃₂O₉
• Molecular Weight: 512.557
• Mol file: 557099-56-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 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)-9,10-diacetyloxy-8,11-dibenzyloxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.03,7]undecane (557099-56-6) → Acetic acid (3R,3aS,4S,5S,6R,6aR)-5-acetoxy-3a,6-bis-benzyloxy-2,3-dihydroxy-hexahydro-cyclopenta[b]furan-4-yl ester

Guidance literature:

With acetic acid; at 90 ℃; for 16h;

DOI:10.1039/b210439c

Reference yield:

(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) → 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 (557099-60-2)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. AcOH / 16 h / 90 °C

2: 200 mg / pyridine / 16 h

3: 65 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 16 h / 50 °C

4: 95 percent / NaOMe / methanol / 16 h / 20 °C

5: 66 percent / p-TsOH*H₂O / acetone / 16 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; acetic acid; In methanol; acetone; acetonitrile;

DOI:10.1039/b210439c

upstream raw materials:

acetic anhydride

(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

Downstream raw materials:

(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

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