(2S,4S)-(+)-cis-4-acetoxyflavan

Base Information

• Chemical Name: (2S,4S)-(+)-cis-4-acetoxyflavan
• CAS No.: 142696-01-3
• Molecular Formula: C₁₇H₁₆O₃
• Molecular Weight: 268.312
• Mol file: 142696-01-3.mol

Synonyms:(2S,4S)-(+)-cis-4-acetoxyflavan

Chemical Property of (2S,4S)-(+)-cis-4-acetoxyflavan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-(+)-cis-4-acetoxyflavan

There total 11 articles about (2S,4S)-(+)-cis-4-acetoxyflavan 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: 40.0%

(+/-)-cis-flavan-4-ol acetate (20755-09-3,20981-69-5,27439-10-7,27439-11-8,65085-03-2,65085-04-3,101521-69-1,142696-01-3) → (2R,4R)-(-)-cis-4-hydroxyflavan (41886-75-3) + (2R,4R)-flavan-4-ol acetate (476310-80-2) + (2S,4S)-(+)-cis-4-acetoxyflavan (142696-01-3)

Guidance literature:

With lipase AY; In phosphate buffer; toluene; at 25 ℃; for 120h;

DOI:10.1271/bbb.66.1772

Reference yield:

Flavanone (487-26-3) → (+/-)-cis-flavan-4-ol acetate (20755-09-3,20981-69-5,27439-10-7,27439-11-8,65085-03-2,65085-04-3,101521-69-1,142696-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1: titanium (III)-chloride; aqueous NH₃

With ammonium hydroxide; titanium(III) chloride;

DOI:10.1002/hlca.19300130612

Reference yield:

FLAVONE (525-82-6,66585-04-4) → (+/-)-cis-flavan-4-ol acetate (20755-09-3,20981-69-5,27439-10-7,27439-11-8,65085-03-2,65085-04-3,101521-69-1,142696-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1: copper oxide-chromium oxide; ethanol / 140 - 150 °C / 73550.8 - 147102 Torr / Hydrogenation

With ethanol; copper oxide-chromium oxide;

DOI:10.1021/ja01270a050

upstream raw materials:

acetic anhydride

cis-4-hydroxyflavan

Flavanone

FLAVONE

Downstream raw materials:

Acetic acid (2S,4S)-2-hydroxy-2-phenyl-chroman-4-yl ester

(2R,3R)-3-hydroxyflavanone

(2R,4R)-(-)-cis-4-hydroxyflavan

(2R,4R)-flavan-4-ol acetate

Refernces

• 1、 Ramadas, Sathunuru,Krupadanam, G.L. David. "Enantioselective acylation of (±)-cis-flavan-4-ols catalyzed by lipase from Candida cylindracea (CCL) and the synthesis of enantiopure flavan-4-ones". . p. 3381 - 3391. Retrieved 2007/10/03.
• 2、 Attwood, Michael R.,Brown, Ben R.,Pike, William T.. "Epimerisation of 4-Acetoxyflavans and Flavan-4-ols". . p. 2229 - 2236. Retrieved 2007/10/02.