(1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadec-5-en-4-one

Base Information

• Chemical Name: (1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadec-5-en-4-one
• CAS No.: 142133-30-0
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445

Synonyms:(1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadec-5-en-4-one

Chemical Property of (1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadec-5-en-4-one

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Technology Process of (1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadec-5-en-4-one

There total 1 articles about (1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.0^2,11.0^3,8>hexadec-5-en-4-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: 15.0%

(1R,3S,4R,5R)-3-<(1S,3E)-1-(benzyloxy)-4-(ethoxycarbonyl)-3-butenyl>-4-(2-oxopropyl)-7,7-dimethyl-2,6,8-trioxabicyclo<3.3.0>octane (142133-20-8) → (1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadec-5-en-4-one (142133-30-0) + (1R,2R,3S,8S,10S,11S,13R)-10-(benzyloxy)-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadecane-4,6-dione (142133-31-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;

DOI:10.1021/jo00042a034

Reference yield:

(1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadec-5-en-4-one (142133-30-0) → C22H28O6 (142235-10-7)

Guidance literature:

Multi-step reaction with 2 steps

2: 78 percent / m-chloroperbenzoic acid

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1021/jo00042a034

Reference yield:

(1R,2R,3S,8R,10S,11S,13R)-10-(benzyloxy)-6-hydroxy-15,15-dimethyl-12,14,16-trioxatetracyclo<11.3.0.02,11.03,8>hexadec-5-en-4-one (142133-30-0) → Acetic acid (3aR,4aS,5S,7S,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 (142133-48-0)

Guidance literature:

Multi-step reaction with 3 steps

2: 78 percent / m-chloroperbenzoic acid

3: 1) lithium aluminum hydride

With lithium aluminium tetrahydride; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1021/jo00042a034

upstream raw materials:

(1R,3S,4R,5R)-3-<(1S,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,6S,6aS,7aR,10aR,10bR,10cS)-6-Benzyloxy-9,9-dimethyl-decahydro-7,8,10-trioxa-pentaleno[1,2-a]naphthalen-1-one

(4aS,6S,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

C₂₂H₂₈O₆

Acetic acid (3aR,4aS,5S,7S,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

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