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

Base Information

• Chemical Name: 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
• CAS No.: 314280-51-8
• Molecular Formula: C₃₁H₃₂O₇
• Molecular Weight: 516.591

Synonyms: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

Chemical Property of 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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Technology Process of 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

There total 2 articles about 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 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: 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

Reference yield:

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) → 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:

Multi-step reaction with 2 steps

1.1: NaBH₄; MeOH / tetrahydrofuran / 0.25 h / 0 °C

1.2: 98 percent / aq. HCl / 2 h

2.1: 93 percent / DMAP / pyridine / 0.25 h / 0 °C

With methanol; dmap; sodium tetrahydroborate; In tetrahydrofuran; pyridine;

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

Reference yield: 95.0%

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) → Acetic acid 6-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-7-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester (314280-52-9)

Guidance literature:

With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.25h;

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

upstream raw materials:

acetic anhydride

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

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 6-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-7-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester

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