Ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenyl-3-hexenoate

Base Information

• Chemical Name: Ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenyl-3-hexenoate
• CAS No.: 844499-09-8
• Molecular Formula: C15H20O3
• Molecular Weight: 248.322
• DSSTox Substance ID: DTXSID201201473
• Nikkaji Number: J2.133.015I
• Mol file: 844499-09-8.mol

Synonyms:DTXSID201201473;844499-09-8;Ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenyl-3-hexenoate

Chemical Property of Ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenyl-3-hexenoate

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 267

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)CC=CC(C)C(C1=CC=CC=C1)O
• Isomeric SMILES: CCOC(=O)C/C=C\[C@@H](C)[C@H](C1=CC=CC=C1)O

Technology Process of Ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenyl-3-hexenoate

There total 1 articles about Ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenyl-3-hexenoate 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%

benzaldehyde (100-52-7) + (E)-(S)-3-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-hex-4-enoic acid ethyl ester (844498-99-3) → ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenylhex-3-enoate (844499-09-8)

Guidance literature:

In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/ejoc.200400572

Reference yield: 53.0%

ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenylhex-3-enoate (844499-09-8) → (2R,3R)-2-methyl-3-phenyl-1,3-propane diol (139068-60-3)

Guidance literature:

ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenylhex-3-enoate; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at 20 ℃;

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 1h; Further stages.;

DOI:10.1002/ejoc.200400572

Reference yield:

ethyl (3Z,5R,6R)-6-hydroxy-5-methyl-6-phenylhex-3-enoate (844499-09-8) → (4R,5R)-5-methyl-2,4-diphenyl-1,3,2-dioxaborinane

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: Me₂S / CH₂Cl₂ / 20 °C

1.3: 53 percent / LiAlH₄ / diethyl ether / 1 h / 20 °C

2.1: 100 percent / CH₂Cl₂ / 20 °C

With ozone; In dichloromethane;

DOI:10.1002/ejoc.200400572

upstream raw materials:

benzaldehyde

(E)-(S)-3-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-hex-4-enoic acid ethyl ester

Downstream raw materials:

(2R,3R)-2-methyl-3-phenyl-1,3-propane diol