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

Base Information

• Chemical Name: 4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one
• CAS No.: 314280-46-1
• Molecular Formula: C₃₀H₃₂O₆
• Molecular Weight: 488.58

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

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

Chemical Property:

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

There total 2 articles about 4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8-dimethoxy-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:

[4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,7,8-trimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yloxy]-tert-butyl-dimethyl-silane → 4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8-dimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one (314280-46-1)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 2h;

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

Reference yield:

4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate (171081-02-0) → 4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8-dimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one (314280-46-1)

Guidance literature:

Multi-step reaction with 2 steps

1: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

2: aq. HF / acetonitrile / 2 h

With n-butyllithium; hydrogen fluoride; In tetrahydrofuran; acetonitrile;

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

Reference yield: 93.0%

4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8-dimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one (314280-46-1) → 6-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-3,7-dimethoxy-3H-isobenzofuran-1-one (314280-47-2)

Guidance literature:

With disodium hydrogenphosphate; magnesium monoperoxyphthalate hexahydrate; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

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

upstream raw materials:

4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate

Downstream raw materials:

6-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-3,7-dimethoxy-3H-isobenzofuran-1-one

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