(E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene

Base Information

Chemical Name:(E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene
CAS No.:883972-97-2
Molecular Formula:C₅₄H₇₆O₁₀Si₂
Molecular Weight:941.362
Hs Code.:

Synonyms:(E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene

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Chemical Property of (E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene

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Technology Process of (E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene

There total 7 articles about (E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene 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: 90.0%

: 883972-88-1
(E,2R,3S,4R,7R,8S,9R)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene-4,7-diol

: 108-24-7
acetic anhydride

: 883972-97-2
(E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 14h;
DOI:10.1002/ejoc.200500614

Reference yield:

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

: 883972-97-2
(E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene

Guidance literature:: Multi-step reaction with 5 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: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; Grubbs catalyst first generation; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
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

: 883972-97-2
(E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene

Guidance literature:: Multi-step reaction with 2 steps

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

2: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 14 h / 20 °C

With dmap; Grubbs catalyst first generation; triethylamine; In dichloromethane;
DOI:10.1002/ejoc.200500614