3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one

Base Information

• Chemical Name: 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one
• CAS No.: 314280-50-7
• Molecular Formula: C₂₉H₃₀O₆
• Molecular Weight: 474.554

Synonyms:3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one

Chemical Property of 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one

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Technology Process of 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one

There total 1 articles about 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one 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: 98.0%

4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one (314280-49-4) → 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one (314280-50-7)

Guidance literature:

4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one; With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 0.25h;

With hydrogenchloride; for 2h;

DOI:10.1016/S0040-4039(00)01478-7

Reference yield: 98.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one (314280-50-7) → 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 1.5h;

DOI:10.1016/S0040-4039(00)01478-7

Reference yield: 93.0%

acetic anhydride (108-24-7) + 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-hydroxy-2-methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one (314280-50-7) → Acetic acid 4-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-methoxy-8-oxo-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl ester (314280-51-8)

Guidance literature:

With dmap; In pyridine; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)01478-7

upstream raw materials:

4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one

Downstream raw materials:

Acetic acid 4-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-methoxy-8-oxo-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl ester

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