(E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

Base Information

Chemical Name:(E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate
CAS No.:883972-93-8
Molecular Formula:C₇₀H₉₀O₁₀
Molecular Weight:1091.48
Hs Code.:

Synonyms:(E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

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Chemical Property of (E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

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Technology Process of (E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

There total 9 articles about (E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate 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: 73.0%

: 883972-91-6
(E,2S,3S,4R,7R,8S,9S)-2,3,4,7,8,9-hexa(benzyloxy)dec-5-ene-1,10-diol

: 106-14-9,18417-00-0,36377-33-0,5762-36-7,78642-86-1,8039-23-4,27924-99-8,860114-96-1
R-12-hydroxyoctadecanoic acid

: 883972-93-8
(E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.200500614

Reference yield:

: (2R,3S,4R)-2,3-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-hex-5-enal

: 883972-93-8
(E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

Guidance literature:: Multi-step reaction with 7 steps

1: 544 mg / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

2: 69 percent / imidazole / dimethylformamide

3: 81 percent / DDQ; water / CH₂Cl₂ / 1 h

4: 66 percent / Grubbs' catalyst / CH₂Cl₂ / 3 h / 40 °C

5: 86 percent / KHMDS / toluene; tetrahydrofuran / -78 - 20 °C

6: 79 percent / tetrahydrofuran; H₂O; acetic acid / 24 h / 50 °C

7: 73 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; CH₂Cl₂

With 1H-imidazole; dmap; lithium aluminium tetrahydride; Grubbs catalyst first generation; 2,4,6-trichlorobenzoyl chloride; water; potassium hexamethylsilazane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene;
DOI:10.1002/ejoc.200500614

Reference yield:

: 883972-87-0
(2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol

: 883972-93-8
(E,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

Guidance literature:: Multi-step reaction with 4 steps

1: 66 percent / Grubbs' catalyst / CH₂Cl₂ / 3 h / 40 °C

2: 86 percent / KHMDS / toluene; tetrahydrofuran / -78 - 20 °C

3: 79 percent / tetrahydrofuran; H₂O; acetic acid / 24 h / 50 °C

4: 73 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / tetrahydrofuran; CH₂Cl₂

With dmap; Grubbs catalyst first generation; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; toluene;
DOI:10.1002/ejoc.200500614