(3S)-3aβ,4,5,6,6aβ,9bα-Hexahydro-3,6,9-trimethyl-6β-hydroxyazuleno[4,5-b]furan-2,8(3H,7H)-dione

Base Information

• Chemical Name: (3S)-3aβ,4,5,6,6aβ,9bα-Hexahydro-3,6,9-trimethyl-6β-hydroxyazuleno[4,5-b]furan-2,8(3H,7H)-dione
• CAS No.: 1618-98-0
• Molecular Formula: C15H20 O4
• Molecular Weight: 264.32
• Mol file: 1618-98-0.mol

Synonyms:5-Azuleneaceticacid, 1,2,4,5,6,7,8,8aa-octahydro-4,8a-dihydroxy-a,3,8-trimethyl-2-oxo-,g-lactone (7CI);Azuleno[4,5-b]furan-2,8(3H,4H)-dione,3a,5,6,6a,7,9b-hexahydro-6-hydroxy-3,6,9-trimethyl-, [3S-(3a,3aa,6a,6aa,9bb)]-; Guai-4-en-12-oic acid, 6a,10-dihydroxy-3-oxo-, g-lactone, (11S)- (8CI);Isophotosantonic lactone (6CI); (11S)-10a-Hydroxy-3-oxoguaia-4-eno-12,6a-lactone; Isophotosantonin;Isosantoxane

Chemical Property of (3S)-3aβ,4,5,6,6aβ,9bα-Hexahydro-3,6,9-trimethyl-6β-hydroxyazuleno[4,5-b]furan-2,8(3H,7H)-dione

Chemical Property:

• PSA: 63.60000
• LogP: 1.61440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S)-3aβ,4,5,6,6aβ,9bα-Hexahydro-3,6,9-trimethyl-6β-hydroxyazuleno[4,5-b]furan-2,8(3H,7H)-dione

There total 9 articles about (3S)-3aβ,4,5,6,6aβ,9bα-Hexahydro-3,6,9-trimethyl-6β-hydroxyazuleno[4,5-b]furan-2,8(3H,7H)-dione 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: 95.0%

O-acetylisophotosantonic lactone (7759-23-1) → (11S)-10α-hydroxy-30-oxoguaia-4-eno-12,6α-lactone (1618-98-0)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃;

DOI:10.5012/bkcs.2012.33.1.289

Reference yield: 75.0%

santonin (481-06-1) → (11S)-10α-hydroxy-30-oxoguaia-4-eno-12,6α-lactone (1618-98-0)

Guidance literature:

With water; acetic acid; at 0 ℃; for 7h; Irradiation; Inert atmosphere;

DOI:10.1021/np300639b

Reference yield:

C24H30N2O6S → (11S)-10α-hydroxy-30-oxoguaia-4-eno-12,6α-lactone (1618-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃*OEt₂ / acetone; H₂O / 108 h / Ambient temperature

2: 5percent aq. potassium hydroxide / 1.25 h

With potassium hydroxide; boron trifluoride diethyl etherate; In water; acetone;

DOI:10.1021/ja00536a036

upstream raw materials:

(3aS)-3c,6,6a-trimethyl-(3ar,6at,9bt)-3a,4,5,6,6a,9b-hexahydro-3H-6c,9ac-cyclo-azuleno[4,5-b]furan-2,7-dione

santonin

O-acetylisophotosantonic lactone

10α-acetoxy-1,7α,5,6,11βH-guaia-3-en-6,12-olide

Downstream raw materials:

C₂₅H₃₄O₅Si

(6R)-6-hydroxydichotoma-3,14-diene-1,17-dial

Toluene-4-sulfonic acid (S)-2-((3aS,4S,5S,8aR)-3-methyl-8-methylene-4-trimethylsilanyloxy-1,3a,4,5,6,7,8,8a-octahydro-azulen-5-yl)-propyl ester

Refernces

• 1、 Chinchilla, Nuria,Santana, Alejandro,Varela, Rosa M.,Fronczek, Frank R.,Molinillo, José M. G.,MacIás, Francisco A.. "Preparation and Phytotoxicity Evaluation of 11,13-Dehydro seco-Guaianolides". . p. 2501 - 2508. Retrieved 2019.
• 2、 Greene. "Highly stereoselective total syntheses of (+)-pachydictyol A and (-)-dictyolene, novel marine diterpenes from Brown seaweeds of the family Dictyotaceae". . p. 5337 - 5343. Retrieved 2007/10/02.