(1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadecane-4,6-dione

Base Information

• Chemical Name: (1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadecane-4,6-dione
• CAS No.: 142186-68-3
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445

Synonyms:(1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadecane-4,6-dione

Chemical Property of (1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadecane-4,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadecane-4,6-dione

There total 1 articles about (1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadecane-4,6-dione 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: 55.0%

(1R,3S,4R,5R)-3-<(1R,3E)-1-(benzyloxy)-4-(ethoxycarbonyl)-3-butenyl>-4-(2-oxopropyl)-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane (142133-21-9) → (1R,2R,3S,8R,10R,11S,13R)-6-hydroxy-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadec-5-ene-4-one (142186-69-4) + (1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadecane-4,6-dione (142186-68-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

DOI:10.1021/jo00042a034

Reference yield:

(1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadecane-4,6-dione (142186-68-3) → Acetic acid (3aR,4aS,5R,7R,8S,8aR,8bR)-7-(4-acetoxy-butyl)-5-benzyloxy-2,2-dimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-8-yl ester (142186-76-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent

2: 1) diisobutylaluminum hydride, 2) aq. acid

3: 65 percent / hydrogen / nickel

4: 41 percent / m-chloroperbenzoic acid

5: 1) lithium aluminum hydride

With lithium aluminium tetrahydride; hydrogen; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; nickel;

DOI:10.1021/jo00042a034

Reference yield:

(1R,2R,3S,8S,10R,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadecane-4,6-dione (142186-68-3) → (4aR,6R,6aS,7aR,10aR,10bR,10cS)-6-Benzyloxy-9,9-dimethyl-decahydro-7,8,10-trioxa-pentaleno[1,2-a]naphthalen-1-one (142186-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent

2: 1) diisobutylaluminum hydride, 2) aq. acid

3: 65 percent / hydrogen / nickel

With hydrogen; diisobutylaluminium hydride; nickel;

DOI:10.1021/jo00042a034

upstream raw materials:

(1R,3S,4R,5R)-3-<(1R,3E)-1-(benzyloxy)-4-(ethoxycarbonyl)-3-butenyl>-4-(2-oxopropyl)-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane

Downstream raw materials:

(4aS,6R,6aS,7aR,10aR,10bR,10cR)-6-Benzyloxy-9,9-dimethyl-4a,5,6,6a,7a,10a,10b,10c-octahydro-4H-7,8,10-trioxa-pentaleno[1,2-a]naphthalen-3-one

(4aR,6R,6aS,7aR,10aR,10bR,10cS)-6-Benzyloxy-9,9-dimethyl-decahydro-7,8,10-trioxa-pentaleno[1,2-a]naphthalen-1-one

C₂₂H₂₈O₆

(4aR,6R,6aS,7aR,10aR,10bR,10cS)-6-Benzyloxy-9,9-dimethyl-4a,5,6,6a,7a,10a,10b,10c-octahydro-4H-7,8,10-trioxa-pentaleno[1,2-a]naphthalen-1-one

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