Ccris 6971

Base Information

• Chemical Name: Ccris 6971
• CAS No.: 37244-00-1
• Molecular Formula: C20H24O8
• Molecular Weight: 392.44
• UNII: 97659Z75CN
• DSSTox Substance ID: DTXSID201043699
• Wikipedia: Vermiculine
• Wikidata: Q104956404
• Mol file: 37244-00-1.mol

Synonyms:vermiculin;vermiculine

Chemical Property of Ccris 6971

Chemical Property:

• Vapor Pressure: 4.73E-17mmHg at 25°C
• Melting Point: 175-177 °C (decomp)
• Refractive Index: 1.4430 (estimate)
• Boiling Point: 655.3°C at 760 mmHg
• Flash Point: 284.7°C
• PSA: 120.88000
• Density: 1.151g/cm³
• LogP: 1.59280
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 392.14711772
• Heavy Atom Count: 28
• Complexity: 641

Purity/Quality:

99% ^*data from raw suppliers

VERMICULINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC1CCC(=O)C=CC(=O)OC(CCC(=O)C=CC(=O)O1)CC(=O)C
• Isomeric SMILES: CC(=O)C[C@H]1OC(=O)/C=C/C(=O)CC[C@H](OC(=O)/C=C/C(=O)CC1)CC(=O)C

Technology Process of Ccris 6971

There total 52 articles about Ccris 6971 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: 83.0%

(3E,5S,8S,11E,13S,16S)-5,13-dihydroxy-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione → (3E,8S,11E,16S)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone (37244-00-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.202105793

Reference yield: 61.0%

(3E,8S,11E,16S)-8,16-di(prop-1-en-1-yl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone → (3E,8S,11E,16S)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone (37244-00-1)

Guidance literature:

With tert.-butylhydroperoxide; silver hexafluoroantimonate; [Pd(quinox)Cl₂]; In 1,2-dichloro-ethane; at 20 ℃; Glovebox; Schlenk technique; Darkness;

DOI:10.1002/chem.201900216

Reference yield:

tert-butyl(((3S)-1-((4S)-2-(4-methoxyphenyl)-1,3-dioxolan-4-yl)hex-5-en-3-yl)oxy)dimethylsilane → (3E,8S,11E,16S)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone (37244-00-1)

Guidance literature:

Multi-step reaction with 12 steps

1: diisobutylaluminium hydride / dichloromethane / 5 h / -78 °C / Inert atmosphere

2: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 20 °C / Inert atmosphere

3: dichloromethane / 2 h

4: hydrogen fluoride; pyridine / tetrahydrofuran / 48 h / 20 °C

5: dmap / toluene / 3 h

6: lithium hydroxide monohydrate / tetrahydrofuran; water / 48 h / 20 °C

7: hydrogen fluoride; pyridine / tetrahydrofuran / 48 h / 20 °C

8: N-ethyl-N,N-diisopropylamine / toluene / 3 h / 20 °C / Inert atmosphere

9: dmap / toluene / 20 °C / Schlenk technique; Inert atmosphere

10: palladium dichloride; copper diacetate / N,N-dimethyl-formamide; water / 48 h / 20 °C

11: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C

12: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / Inert atmosphere

With pyridine; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; hydrogen fluoride; copper diacetate; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.202105793

upstream raw materials:

(3E,11E)-(8S,16S)-8,16-Diallyl-1,9-dioxa-cyclohexadeca-3,11-diene-2,5,10,13-tetraone

1,2:5,6-dianhydro-3,4-dideoxy-erythro-hexitol

(5S,8S)-Dodeca-1,11-diene-5,8-diol

(5S,8S)-8-Benzyloxy-dodeca-1,11-dien-5-ol

Downstream raw materials:

<2E,7E>-4,9-Dioxo-2,7-decadienoic acid

<2E,2'E,-7S,7'E>-4,9-dioxo-7-(4',9'-dioxo-2',7'-decadienoyloxy)-2-decenoic acid

<8S,16S>-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-2,5,10,13-tetraone

<8S,13RS,16S>-8,16-bis(2-oxopropyl)-13-hydroxy-1,9-dioxacyclohexadeca-2,5,10-trione

Refernces

• 1、 Steib, Philip,Breit, Bernhard. "Concise Total Synthesis of (?)-Vermiculine through a Rhodium-Catalyzed C2-Symmetric Dimerization Strategy". . p. 3532 - 3535. Retrieved 2019/02/19.
• 2、 Wakamatsu, Takeshi,Yamada, Satoshi,Ban, Yoshio. "SYNTHESIS OF dl-VERMICULINE VIA CONTROL OF OLEFIN FORMATION". . p. 309 - 312. Retrieved 2007/10/02.