L-xylo-Heptonic acid,2,3,5,6,7-pentadeoxy-3,6-epidioxy-4-C-methyl-6-C-(10-phenyldecyl)-, g-lactone (9CI)

Base Information

• Chemical Name: L-xylo-Heptonic acid,2,3,5,6,7-pentadeoxy-3,6-epidioxy-4-C-methyl-6-C-(10-phenyldecyl)-, g-lactone (9CI)
• CAS No.: 162559-02-6
• Molecular Formula: C24H36 O4
• Molecular Weight: 388.547
• Mol file: 162559-02-6.mol

Synonyms:Furo[3,2-c]-1,2-dioxin-6(3H)-one,tetrahydro-3,4a-dimethyl-3-(10-phenyldecyl)-, [3R-(3a,4aa,7aa)]-; Plakortolide E

Chemical Property of L-xylo-Heptonic acid,2,3,5,6,7-pentadeoxy-3,6-epidioxy-4-C-methyl-6-C-(10-phenyldecyl)-, g-lactone (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-xylo-Heptonic acid,2,3,5,6,7-pentadeoxy-3,6-epidioxy-4-C-methyl-6-C-(10-phenyldecyl)-, g-lactone (9CI)

There total 31 articles about L-xylo-Heptonic acid,2,3,5,6,7-pentadeoxy-3,6-epidioxy-4-C-methyl-6-C-(10-phenyldecyl)-, g-lactone (9CI) 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: 42.0%

(5R)-5-methyl-5-(12-phenyl-2-methylenedodec-1-yl)-3-oxolen-2-one → (+)-plakortolide E (162559-02-6) + 4,6-dimethyl-4-hydroxy-3,6-peroxy-16-phenylhexadecanoic acid 1,4-lactone

Guidance literature:

(5R)-5-methyl-5-(12-phenyl-2-methylenedodec-1-yl)-3-oxolen-2-one; With triethylsilane; oxygen; bis(2,2,6,6-tetramethyl-3,5-heptadionato) copper(II); In 1,2-dichloro-ethane; isopropyl alcohol; at 0 ℃; for 28h; Schlenk technique;

With 2,2,2-trifluoroethanol; tetrabutyl ammonium fluoride; In 1,2-dichloro-ethane; isopropyl alcohol; at -5 - 0 ℃; for 0.25h; Schlenk technique;

DOI:10.1021/acs.orglett.1c01457

Reference yield: 34.0%

(2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate (1353566-43-4) → (+)-plakortolide E (162559-02-6) + (1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one (1353566-51-4) + 4,6-dimethyl-4-hydroxy-3,6-peroxy-16-phenylhexadecanoic acid 1,4-lactone

Guidance literature:

(2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 3h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 2,2,2-trifluoroethanol; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol203185f

Reference yield: 29.0%

(2R,3R)-2-methyl-2-(2-methyl-12-phenyl-2-((triethylsilyl)peroxy)dodecyl)-5-oxotetrahydrofuran-3-yl acetate (1353566-43-4) → (+)-plakortolide E (162559-02-6) + (1S,4R,5R)-4-(2-hydroxy-2-methyl-12-phenyldodecyl)-4-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-one (1353566-51-4) + C30H50O4Si (1353566-52-5) + 4,6-dimethyl-4-hydroxy-3,6-peroxy-16-phenylhexadecanoic acid 1,4-lactone

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/ol203185f

upstream raw materials:

1 ,6-dibromohexane

(R)-2-methyl-4-methylene-14-phenyl-1-((triethylsilyl)oxy)tetradecan-2-ol

(R)-3,3,8,8-tetraethyl-5-methyl-5-(2-methylene-12-phenyldodecyl)-4,7-dioxa-3,8-disiladecane

(R)-2-methyl-4-methylene-14-phenyl-2-((triethylsilyl)oxy)tetradecan-1-ol

Downstream raw materials:

(4R,5R)-4-hydroxy-5-((R)-2-hydroxy-2-methyl-12-phenyldodecyl)-5-methyldihydrofuran-2(3H)-one

Refernces

• 1、 Barnych, Bogdan,Vatele, Jean-Michel. "Total synthesis of seco-plakortolide e and (-)-ent-plakortolide I: Absolute configurational revision of natural plakortolide i". . p. 564 - 567. Retrieved 2012/03/26.