(2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

Base Information

Chemical Name:(2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol
CAS No.:251319-59-2
Molecular Formula:C₂₈H₅₀O₆Si₂
Molecular Weight:538.872
Hs Code.:

Synonyms:(2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

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Chemical Property of (2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

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Technology Process of (2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

There total 12 articles about (2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol 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: 80.0%

: 65-85-0,8013-63-6
benzoic acid

: 251319-58-1
{(2R,3S)-3-[(Z)-(1R,2S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enyl]-oxiranyl}-methanol

: 251319-59-2
(2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

Guidance literature:: With titanium(IV) isopropylate; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(99)01481-1

Reference yield: 80.0%

: 65-85-0,8013-63-6
benzoic acid

: (2R,3S,4R,5R,6Z)-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1-ol

: 251319-59-2
(2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

Guidance literature:: With titanium(IV) isopropylate; In tetrahydrofuran; for 18h;
DOI:10.1016/S0040-4020(00)00804-8

Reference yield:

: 251319-56-9
(2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al

: 251319-59-2
(2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

2: 100 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

3: 97 percent / imidazole / dimethylformamide / 0.17 h

4: 97 percent / di-tert-butylbiphenyllithium / tetrahydrofuran / -78 °C

5: 82 percent / (-)-diethyltartrate; t-BuOOH; titanium(IV) isopropoxide / CH₂Cl₂ / 18 h / -28 °C

6: 80 percent / titanium(IV) isopropoxide / tetrahydrofuran / 18 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium 4,4′-di-tert-butylbiphenylide; (-)-diethyl tartrate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Reduction / 3: Substitution / 4: Elimination / 5: Epoxidation / 6: Ring cleavage;
DOI:10.1016/S0040-4020(00)00804-8