9-[(2S,3R,6E)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-one

Base Information

• Chemical Name: 9-[(2S,3R,6E)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-one
• CAS No.: 67359-28-8
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.488
• DSSTox Substance ID: DTXSID001318335
• ChEMBL ID: CHEMBL166575
• Mol file: 67359-28-8.mol

Synonyms:CHEMBL166575;SCHEMBL11105337;DTXSID001318335;67359-28-8

Chemical Property of 9-[(2S,3R,6E)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-one

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 338.24570956
• Heavy Atom Count: 24
• Complexity: 462

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCCC1(C(CCC(=CCO)CO1)O)C)C(=O)CC=C(C)C
• Isomeric SMILES: CC(CCC[C@]1([C@@H](CC/C(=C\CO)/CO1)O)C)C(=O)CC=C(C)C

Technology Process of 9-[(2S,3R,6E)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-one

There total 81 articles about 9-[(2S,3R,6E)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-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: 90.0%

(2S,3R)-6-[2-Hydroxy-eth-(E)-ylidene]-2-methyl-2-{4-[2-(3-methyl-but-2-enyl)-[1,3]dioxolan-2-yl]-pentyl}-oxepan-3-ol → (+/-)-zoapatanol (67359-28-8,71117-51-6,73465-97-1,75419-15-7,75419-19-1,78039-31-3)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 38 ℃; for 18h;

DOI:10.1021/ja00541a063

Reference yield: 80.0%

(2SR,3RS,6E)-3-t-butyldimethylsiloxy-(2-t-butyldimethylsiloxyethilidene)-2-(4,8-dimethyl-5-oxo-non-7-enyl)-2-methyloxepane (100582-59-0,121840-81-1,121840-82-2) → (+/-)-zoapatanol (67359-28-8,71117-51-6,73465-97-1,75419-15-7,75419-19-1,78039-31-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 2h; Ambient temperature;

Reference yield: 30.0%

3-methyl-2-butenyllithium (50585-10-9,86211-76-9) + 5-{(2S,3R)-3-Hydroxy-6-[2-hydroxy-eth-(E)-ylidene]-2-methyl-oxepan-2-yl}-2-methyl-pentanoic acid → (+/-)-zoapatanol (67359-28-8,71117-51-6,73465-97-1,75419-15-7,75419-19-1,78039-31-3)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/ja00541a062

upstream raw materials:

Acetic acid (2S,3R)-6-[2-acetoxy-eth-(Z)-ylidene]-2-(4,8-dimethyl-5-oxo-non-7-enyl)-2-methyl-oxepan-3-yl ester

4-bromo-2-methylbut-1-ene

Acetic acid (2S,3R)-2-(5-hydroxy-4,8-dimethyl-non-7-enyl)-2-methyl-6-oxo-oxepan-3-yl ester

5-((8S,9R)-9-Benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-2-methyl-pentanal

Downstream raw materials:

C₃₄H₄₀Br₂O₆

(10S,11R)-10,11-dihydroxy-5-(p-toluenesulfonylhydrazino)-2,6,10,14-tetramethylhexadecane

(1'S,4'S,5'R)-1'-ethyl-4'-(4,8-dimethyl-5-oxononyl)-4'-methyl-3',8'-dioxabicyclo<3.2.1>octane p-toluenesulfonylhydrazone

(1'S,4'S,5'R)-1'-ethyl-4'-(4,8-dimethyl-5-oxononyl)-4'-methyl-3',8'-dioxabicyclo<3.2.1>octane (p-bromobenzenesulfonyl)hydrazone