endo rocaglic acid

Base Information

• Chemical Name: endo rocaglic acid
• CAS No.: 190385-15-0
• Molecular Formula: C₂₇H₂₆O₈
• Molecular Weight: 478.499
• Mol file: 190385-15-0.mol

Synonyms:endo rocaglic acid

Chemical Property of endo rocaglic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo rocaglic acid

There total 20 articles about endo rocaglic acid 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: 97.0%

aglafoline (143901-35-3) → endo rocaglic acid (190385-15-0)

Guidance literature:

With potassium hydroxide; In methanol; water; at 60 ℃;

DOI:10.1016/j.bmcl.2015.12.045

Reference yield: 57.0%

(-)-rocaglaic acid-(L)-menthyl ester → endo rocaglic acid (190385-15-0)

Guidance literature:

With water; sodium hydroxide; In dimethyl sulfoxide; at 60 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm201263k

Reference yield:

keto rocaglate (901774-46-7) → endo rocaglic acid (190385-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Me₄NBH(OAc)3; acetic acid / acetonitrile / 3 h / 20 °C

2: 96 percent / potassium hydroxide / methanol / 12 h / 44 °C

With potassium hydroxide; acetic acid; tetramethylammonium triacetoxyborohydride; In methanol; acetonitrile;

DOI:10.1021/ja062621j

upstream raw materials:

aglafoline

keto rocaglate

1-[4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3-yl]-3-phenylprop-2-yn-1-ol

3-(1-(4-methoxybenzyloxy)-3-phenylprop-2-ynyl)-4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran

Downstream raw materials:

rocaglamide

(?)-CR-1-31-B

(-)-(2aR,3S,3aR,8bS,8cR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-3,3a,8b,8c-tetrahydro-oxeto[2',3':3,4]cyclopenta[1,2-b]benzofuran-2(2aH)-one

Refernces

• 1、 Chambers, Jennifer M.,Lindqvist, Lisa M.,Savage, G. Paul,Rizzacasa, Mark A.. "Total synthesis of a biotinylated rocaglate: Selective targeting of the translation factors eIF4AI/II". . p. 262 - 264. Retrieved 2016.
• 2、 Malona, John A.,Cariou, Kevin,Spencer, William T.,Frontier, Alison J.. "Total synthesis of (±)-rocaglamide via oxidation-initiated nazarov cyclization". experimental part. p. 1891 - 1908. Retrieved 2012/04/23.