9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene

Base Information

• Chemical Name: 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene
• CAS No.: 356031-77-1
• Molecular Formula: C₄₈H₅₆O₁₁
• Molecular Weight: 808.966

Synonyms:9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene

Chemical Property of 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene

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Technology Process of 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene

There total 4 articles about 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene 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: 81.0%

2-chloro-1,4-dimethoxybenzene (2100-42-7) + C40H48O9 (356031-76-0) → 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene (356031-77-1)

Guidance literature:

With sec.-butyllithium; at -95 - 25 ℃;

DOI:10.1021/ja0108640

Reference yield:

(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one (79999-46-5,72605-77-7) → 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene (356031-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi

1.3: 58 percent / NaCNBH₃; HCl / ethanol

2.1: 81 percent / sec-BuLi / -95 - 25 °C

With n-butyllithium; sec.-butyllithium;

DOI:10.1021/ja0108640

Reference yield:

O3,O4,O6-trimethyl-D-arabino-2-deoxy-hexonic acid-lactone (51224-22-7) → 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene (356031-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA

1.3: 55 percent / NaCNBH₃; HCl / ethanol

2.1: n-BuLi

2.3: 58 percent / NaCNBH₃; HCl / ethanol

3.1: 81 percent / sec-BuLi / -95 - 25 °C

With n-butyllithium; sec.-butyllithium; lithium diisopropyl amide;

DOI:10.1021/ja0108640

upstream raw materials:

2-chloro-1,4-dimethoxybenzene

C₄₀H₄₈O₉

(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one

O³,O⁴,O⁶-trimethyl-D-arabino-2-deoxy-hexonic acid-lactone

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