(+)-Leucocyanidin

Base Information

• Chemical Name: (+)-Leucocyanidin
• CAS No.: 69256-15-1
• Deprecated CAS: 17277-70-2
• Molecular Formula: C15H14O7
• Molecular Weight: 306.272
• Nikkaji Number: J1.901.199B
• Wikidata: Q23419096
• ChEMBL ID: CHEMBL126393
• Mol file: 69256-15-1.mol

Synonyms:(+)-Leucocyanidin;(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,4,5,7-tetrol;69256-15-1;2,3-trans-3,4-trans-leucocyanidin;(2R,3S,4R)-leucocyanidin;CHEMBL126393;Q23419096;(2r,3s,4r)-(+)-3,4,5,7,3',4'-hexahydroxyflavan;2H-1-Benzopyran-3,4,5,7-tetrol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-(2alpha,3beta,4alpha))-

Chemical Property of (+)-Leucocyanidin

Chemical Property:

• Vapor Pressure: 2.46E-17mmHg at 25°C
• Melting Point: >300℃
• Boiling Point: 641.5°C at 760 mmHg
• Flash Point: 341.8°C
• PSA: 130.61000
• Density: 1.709
• LogP: 1.03700
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 306.07395278
• Heavy Atom Count: 22
• Complexity: 392

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2C(C(C3=C(C=C(C=C3O2)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@@H]2[C@H]([C@@H](C3=C(C=C(C=C3O2)O)O)O)O)O)O

Technology Process of (+)-Leucocyanidin

There total 10 articles about (+)-Leucocyanidin 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: 75.0%

taxifolin (480-18-2,17654-26-1,5117-01-1) → (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan (69256-15-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 2h;

Reference yield:

catechin (154-23-4) → (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan (69256-15-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: K₂CO₃ / dimethylformamide / 3 h / 130 °C

1.2: 81 percent / NaH / dimethylformamide / 3 h / 20 °C

2.1: 85 percent / Pb₃O₄ / benzene / 3 h / 75 - 80 °C

3.1: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 2 h / 20 °C

4.1: 85 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; MgSO₄ / CH₂Cl₂ / 3 h / 20 °C

5.1: 90 percent / H₂ / Pd/C / methanol; tetrahydrofuran / 24 h / 20 °C

6.1: 75 percent / NaBH₄ / ethanol / 2 h / 20 °C

With sodium tetrahydroborate; tetrapropylammonium perruthennate; lead(II,IV) oxide; hydrogen; magnesium sulfate; potassium carbonate; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

(2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman (85443-49-8) → (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan (69256-15-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / Pb₃O₄ / benzene / 3 h / 75 - 80 °C

2: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 2 h / 20 °C

3: 85 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; MgSO₄ / CH₂Cl₂ / 3 h / 20 °C

4: 90 percent / H₂ / Pd/C / methanol; tetrahydrofuran / 24 h / 20 °C

5: 75 percent / NaBH₄ / ethanol / 2 h / 20 °C

With sodium tetrahydroborate; tetrapropylammonium perruthennate; lead(II,IV) oxide; hydrogen; magnesium sulfate; potassium carbonate; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; benzene;

upstream raw materials:

taxifolin

methanol

(2R^*,3S^*,4R^*)-5,7,3',4'-tetramethoxyflavan-3,4-diol

catechin

Downstream raw materials:

cyanidin

quercetol

(-)-epitaxifolin

taxifolin

Refernces

• 1、 Turnbull, Jonathan J.,Nagle, Michael J.,Seibel, Juergen F.,Welford, Richard W. D.,Grant, Guy H.,Schofield, Christopher J.. "The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity". . p. 3853 - 3857. Retrieved 2003.
• 2、 Zyl, Pieter W. van,Steynberg, Jan P.,Brandt, Edward V.,Ferreira, Daneel. "Spectroscopic Properties of Free Phenolic 4-Arylflavan-3-ols as Models for Natural Condensed Tannins". . p. 1057 - 1063. Retrieved 2007/10/02.