(1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.0^2,4]undecane

Base Information

• Chemical Name: (1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.0^2,4]undecane
• CAS No.: 111596-69-1
• Molecular Formula: C₂₉H₄₄O₆
• Molecular Weight: 488.665

Synonyms:(1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.0^2,4]undecane

Chemical Property of (1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.0^2,4]undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.0^2,4]undecane

There total 1 articles about (1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.0^2,4]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: 94.0%

(1S,2S,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-7-(tetrahydro-pyran-2-yloxy)-bicyclo[4.3.1]decan-2-ol (111596-70-4) → (1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.02,4]undecane (111596-69-1)

Guidance literature:

With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25 ℃;

DOI:10.1016/S0040-4039(00)96035-0

Reference yield: 92.0%

(1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.02,4]undecane (111596-69-1) → (1S,2S,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-7-(tetrahydro-pyran-2-yloxy)-bicyclo[4.3.1]decan-2-ol (111596-70-4)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(00)96035-0

Reference yield:

(1R,4R,6S,7S,8S,11R)-6-((R)-4-Benzyloxy-1-methyl-butyl)-11-methoxymethoxy-8-(tetrahydro-pyran-2-yloxy)-3-oxa-tricyclo[5.3.1.02,4]undecane (111596-69-1) → (1S,5S,10R)-5-((R)-1,5-Dimethyl-hex-4-enyl)-10-methoxymethoxy-2-methylene-8-phenylsulfanyl-bicyclo[4.3.1]decan-7-one (113432-77-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / DIBAH / toluene / -78 - 0 °C

2: 86 percent / PDC

3: 1.) n-BuLi / 2.) THF, 0 deg C

4: 93 percent / Li, liq. NH₃ / tetrahydrofuran / -34 °C

5: 82 percent / PDC

6: 1.)n-BuLI / 2.) THF, 0 deg C

7: 91 percent / AcOH, H₂O / 40 °C

8: 88 percent / PDC

9: 71 percent / LDA / -78 °C

With dipyridinium dichromate; n-butyllithium; ammonia; water; lithium; diisobutylaluminium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(00)96035-0

upstream raw materials:

(1S,2S,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-7-(tetrahydro-pyran-2-yloxy)-bicyclo[4.3.1]decan-2-ol

Downstream raw materials:

Acetic acid (1S,3R,6R,7R,9S,11S)-9-((R)-4-benzyloxy-1-methyl-butyl)-7-methoxymethoxy-2-oxa-tricyclo[4.4.1.0^3,8]undec-11-yl ester

(1S,2S,5R,7R,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-7-(tetrahydro-pyran-2-yloxy)-bicyclo[4.3.1]decan-2-ol

(1S,5S,10R)-5-((R)-1,5-Dimethyl-hex-4-enyl)-10-methoxymethoxy-2-methylene-8-phenylsulfanyl-bicyclo[4.3.1]decan-7-one

2-[(1R,5R,7S,10S)-5-((S)-4-Benzyloxy-1-methyl-butyl)-10-methoxymethoxy-2-methylene-bicyclo[4.3.1]dec-7-yloxy]-tetrahydro-pyran

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