(3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

Base Information

Chemical Name:(3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one
CAS No.:1445989-80-9
Molecular Formula:C₂₀H₂₅NO₂S₂
Molecular Weight:375.556
Hs Code.:

Synonyms:(3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

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Chemical Property of (3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

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Technology Process of (3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

There total 11 articles about (3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one 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: 75.0%

: 911040-42-1
1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone

: 139026-03-2
(E)-4-Methyl-4,6-heptadienal

: 1445989-81-0
(S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

: 1445989-80-9
(3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

Guidance literature:: With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 7h; stereoselective reaction;
DOI:10.1016/j.tetlet.2013.06.071

Reference yield: 55.0%

: 911040-42-1
1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone

: 139026-03-2
(E)-4-Methyl-4,6-heptadienal

: 1445989-80-9
(3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

Guidance literature:: 1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone; With titanium tetrachloride; In dichloromethane; at -40 ℃; for 0.0833333h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -40 ℃; for 1h; Inert atmosphere;

(E)-4-Methyl-4,6-heptadienal; In dichloromethane; at -78 ℃; for 0.333333h; Inert atmosphere;
DOI:10.3390/md15010017

Reference yield:

: 141-27-5,96680-15-8
3,7-dimethyl-2,6-octadienal

: 1445989-80-9
(3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C / Inert atmosphere

2.1: methyltriphenyl-lambda5-phosphane hydrobromide; n-butyllithium / tetrahydrofuran / 0 °C / Inert atmosphere

3.1: periodic acid / tetrahydrofuran; water / 0 °C / Inert atmosphere

4.1: titanium tetrachloride / dichloromethane / 0.08 h / -40 °C / Inert atmosphere

4.2: 1 h / -40 °C / Inert atmosphere

4.3: 0.33 h / -78 °C / Inert atmosphere

With n-butyllithium; methyltriphenyl-lambda5-phosphane hydrobromide; titanium tetrachloride; periodic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water; 2.1: |Wittig Olefination;
DOI:10.3390/md15010017