(±)-Hyalodendrin

Base Information

• Chemical Name: (±)-Hyalodendrin
• CAS No.: 53777-19-8
• Molecular Formula: C14H16N2O3S2
• Molecular Weight: 0
• Mol file: 53777-19-8.mol

Synonyms:2,2'-disulfanediyl-N,N'-dimethyl-cyclo-(DL-phenylalanyl->DL-seryl);(+/-)-Hyalodendrin;dl- Hyalodendrin;(1R,4R)-1-Benzyl-4-hydroxymethyl-5,7-dimethyl-2,3-dithia-5,7-diaza-bicyclo[2.2.2]octane-6,8-dione;1-benzyl-4-hydroxymethyl-5,7-dimethyl-2,3-dithia-5,7-diaza-bicyclo[2.2.2]octane-6,8-dione;

Chemical Property of (±)-Hyalodendrin

Chemical Property:

• Melting Point: 101 - 102 °C (ethanol)
• PSA: 111.45000
• LogP: 0.81520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (±)-Hyalodendrin

There total 29 articles about (±)-Hyalodendrin 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: 70.0%

C33H32N2O4S2 → (±)-hyalodendrin (53777-19-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01770

Reference yield: 22.0%

3-(4-methoxyphenyl)-6,8-dimethyl-1-hydroxymethyl-5-(phenylmethyl)-2,4-dithia-6,8-diazabicyclo[3.2.2]nonaiie-7,9-dione → 1,4-dimethyl-3-hydroxymethyl-6-phenylmethyl-2,5-piperazinedione-3,6-disulfide (51920-94-6,40380-24-3,51773-88-7,53777-19-8)

Guidance literature:

3-(4-methoxyphenyl)-6,8-dimethyl-1-hydroxymethyl-5-(phenylmethyl)-2,4-dithia-6,8-diazabicyclo[3.2.2]nonaiie-7,9-dione; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.166667h;

With perchloric acid; dimethylsulfide; In methanol; dichloromethane; at 0 - 20 ℃; for 9h;

Reference yield:

6-benzyl-6-((((tert-butyldimethylsilyl)oxy)methyl)thio)-1,4-dimethylpiperazine-2,3,5-trione → (±)-hyalodendrin (53777-19-8)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

3: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 5 h / 20 °C

5: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

With osmium(VIII) oxide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/acs.orglett.9b01770

upstream raw materials:

3r-benzyl-6c-hydroxymethyl-3,6t-bis-methoxymethylsulfanyl-1,4-dimethyl-piperazine-2,5-dione

(3S,6S)-3-Benzyl-6-methoxymethyl-3,6-bis-methoxymethylsulfanyl-1,4-dimethyl-piperazine-2,5-dione

benzyl bromide

(3R,6R)-3,6-Bis-methoxymethylsulfanyl-1,4-dimethyl-piperazine-2,5-dione

Downstream raw materials:

1-benzyl-6-hydroxymethyl-7,9-dimethyl-2,3,4,5-tetrathia-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

(1S)-1-benzyl-6-hydroxymethyl-7,9-dimethyl-2,3,4,5-tetrathia-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

Refernces

• 1、 Szulc, Blanka R.,Sil, Bruno C.,Ruiz, Arnaud,Hilton, Stephen T.. "A Common Precursor Approach to Structurally Diverse Natural Products: The Synthesis of the Core Structure of (±)-Clausenamide and the Total Synthesis of (±)-Hyalodendrin". . p. 7438 - 7442. Retrieved 2016/01/26.
• 2、 Fukuyama, Tohru,Nakatsuka, Shin-Ichi,Kishi, Yoshito. "TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN". . p. 2045 - 2078. Retrieved 2007/10/02.