(3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione

Base Information

• Chemical Name: (3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione
• CAS No.: 1668-07-1
• Molecular Formula: C₁₃H₁₂N₂O₄S₂
• Molecular Weight: 324.381
• Mol file: 1668-07-1.mol

Synonyms:10H-3,10a-Epidithiopyrazino[1,2-a]indole-1,4-dione,2,3-dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-, (3R)- (8CI); Gliotoxin,dehydro- (7CI); Anhydrogliotoxin; Dehydrogliotoxin

Chemical Property of (3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione

Chemical Property:

• Vapor Pressure: 1.55E-19mmHg at 25°C
• Boiling Point: 682°Cat760mmHg
• Flash Point: 366.3°C
• PSA: 131.68000
• Density: 1.81g/cm³
• LogP: 0.53610

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione

There total 23 articles about (3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-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:

gliotoxin (67-99-2) → 5a,6-didehydrogliotoxin (50763-58-1,1668-07-1,7776-21-8)

Guidance literature:

With o-tetrachloroquinone; In benzene;

DOI:10.1039/jr9640004315

Reference yield:

3-methoxy-2-[3ξ-(4-methoxy-phenyl)-8-methyl-7,9-dioxo-2,4-dithia-6,8-diaza-bicyclo[3.2.2]non-6-yl]-benzoic acid methyl ester (50627-34-4,50894-22-9,79355-30-9) → dl-dehydrogliotoxin (1668-07-1,50763-58-1,7776-21-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1N NaOH / dioxane / 3 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 10 h / Ambient temperature

3: NaBH₄ / methanol; CH₂Cl₂ / 0.08 h / 0 °C

4: 1.) CH₃SO₂Cl, Et₃N; 2.) LiCl / 1.) CH₂Cl₂, r.t. 10 min; 2.) DMF, r.t., 15 min.

5: 72.5 percent / phenyllithium / tetrahydrofuran / 0.17 h / -78 °C

6: 93.8 percent / phenyllithium / tetrahydrofuran / -78 °C

7: 66.2 percent / BCl₃ / CH₂Cl₂ / 0.33 h / Ambient temperature

8: 1.) mClPBA; 2.) dimethylsulfide, perchloric acid / 1.) CH₂Cl₂, r.t., 5 min; 2.) CH₂Cl₂, MeOH, 7 h

With sodium hydroxide; sodium tetrahydroborate; perchloric acid; dimethylsulfide; boron trichloride; methanesulfonyl chloride; phenyllithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)97960-8

Reference yield:

(1R,3R,5R)-6-(2-Chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione (49593-04-6,49593-05-7,50763-59-2,50763-60-5) → dl-dehydrogliotoxin (1668-07-1,50763-58-1,7776-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 72.5 percent / phenyllithium / tetrahydrofuran / 0.17 h / -78 °C

2: 93.8 percent / phenyllithium / tetrahydrofuran / -78 °C

3: 66.2 percent / BCl₃ / CH₂Cl₂ / 0.33 h / Ambient temperature

4: 1.) mClPBA; 2.) dimethylsulfide, perchloric acid / 1.) CH₂Cl₂, r.t., 5 min; 2.) CH₂Cl₂, MeOH, 7 h

With perchloric acid; dimethylsulfide; boron trichloride; phenyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)97960-8

upstream raw materials:

gliotoxin

C₂₁H₂₀N₂O₅S₂

C₂₁H₂₀N₂O₅S₂

1-methylpiperazin-2,5-dione

Refernces

• 1、 Johns, Nicholas,Kirby, Gordon W.. "The Biosynthetic Incorporation of Phenylalanine into Gliotoxin". . p. 1487 - 1490. Retrieved 2007/10/02.