Dibenzylbutyrolactone

Base Information

• Chemical Name: Dibenzylbutyrolactone
• CAS No.: 34444-37-6
• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.39
• NSC Number: 266185
• Wikidata: Q105377453
• ChEMBL ID: CHEMBL1483370
• Mol file: 34444-37-6.mol

Synonyms:8'-(R)-4,4',8-trihydroxy-3,3'-dimethoxylignanolide;dihydro-3-hydroxy-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-2(3H)-furanone;nortrachelogenin;nortrachelogenin, (3R-cis)-isomer;wikstromol

Chemical Property of Dibenzylbutyrolactone

Chemical Property:

• Vapor Pressure: 1.08E-15mmHg at 25°C
• Refractive Index: 1.629
• Boiling Point: 609.1 °C at 760 mmHg
• Flash Point: 217.3 °C
• PSA: 105.45000
• Density: 1.37 g/cm³
• LogP: 1.80430
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 374.13655304
• Heavy Atom Count: 27
• Complexity: 513

Purity/Quality:

99% ^*data from raw suppliers

Nortrachelogenin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)O

Technology Process of Dibenzylbutyrolactone

There total 27 articles about Dibenzylbutyrolactone 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: 98.0%

(2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide (124988-56-3) → (-)-nortrachelogenin (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 20h;

DOI:10.1021/jo001547z

Reference yield: 85.0%

dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone (116185-15-0,116185-17-2,124988-56-3,124988-57-4,124988-60-9,124988-61-0) → epiwikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7) + wikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 20h; under 760 Torr;

DOI:10.1021/jo00255a012

Reference yield: 85.0%

dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone (116185-15-0,116185-17-2,124988-56-3,124988-57-4,124988-60-9,124988-61-0) → epiwikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7) + wikstromol (34444-37-6,61521-74-2,116261-31-5,116261-33-7,124988-62-1,125072-69-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 20h; under 760 Torr;

DOI:10.1021/jo00255a012

upstream raw materials:

(2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide

1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene

(R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone

(3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one

Downstream raw materials:

7-hydroxysecoisolariciresinol

3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone

3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone

(-)-O-methyltrachelogenine

Refernces

• 1、 Sefkow. "Enantioselective synthesis of (-)-wikstromol using a new approach via malic acid". . p. 2343 - 2349. Retrieved 2007/10/03.
• 2、 Khamlach, Kenza,Dhal, Robert,Brown, Eric. "TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL". . p. 2221 - 2224. Retrieved 2007/10/02.