9-deoxygoniopypyrone

Base Information

• Chemical Name: 9-deoxygoniopypyrone
• CAS No.: 136685-37-5
• Molecular Formula: C13H14 O4
• Molecular Weight: 234.252
• Mol file: 136685-37-5.mol

Synonyms:2,6-Dioxabicyclo[3.3.1]nonane,D-xylo-heptonic acid deriv.; (+)-9-Deoxygoniopypyrone; 9-Deoxygoniopypyrone

Chemical Property of 9-deoxygoniopypyrone

Chemical Property:

• Vapor Pressure: 6.66E-10mmHg at 25°C
• Boiling Point: 476.9°Cat760mmHg
• Flash Point: 189.2°C
• PSA: 55.76000
• Density: 1.298g/cm³
• LogP: 1.19300

Purity/Quality:

99% ^*data from raw suppliers

9-Deoxygoniopypyrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9-deoxygoniopypyrone

There total 59 articles about 9-deoxygoniopypyrone 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%

(R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one (214678-61-2) → (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one (136685-37-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(98)01562-7

Reference yield: 96.0%

(-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one (194355-10-7) → (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one (136685-37-5)

Guidance literature:

With titanium tetrachloride; In dichloromethane;

DOI:10.1021/jo970725u

Reference yield: 92.0%

(R)-goniothalamin (22639-28-7,57885-00-4,118204-01-6,122046-62-2,17303-67-2) → (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one (136685-37-5)

Guidance literature:

With (DHQ)2-PHAL; potassium carbonate; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); In tert-butyl alcohol; at 0 ℃; for 20h;

upstream raw materials:

(R)-6-((R)-2-Hydroxy-1-methoxymethoxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

(6R)-6-[(1R,2S)-1,2-dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one

(-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

(R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one

Refernces

• 1、 Prasad, Kavirayani R.,Dhaware, Madhuri G.. "Stereoselective total synthesis of bioactive styryllactones: 9-Deoxygoniopypyrone, goniopypyrone and 7-epi-goniofufurone". . p. 3697 - 3705. Retrieved 2008/09/19.
• 2、 Liu, Zhi-Yu,Ji, Jian-Xin,Li, Bo-Gang. "Efficient synthesis of the styryllactones, (+)-goniothalamin, (+)-7-epi-goniodiol and (+)-9-deoxygoniopypyrone". . p. 61 - 63. Retrieved 2007/10/03.