11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol

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Chemical Name:11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol
CAS No.:100311-71-5
Molecular Formula:C₃₇H₄₈O₅Si
Molecular Weight:600.871
Hs Code.:
Mol file:100311-71-5.mol

Synonyms:11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol

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Chemical Property of 11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol Edit

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Technology Process of 11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol

There total 6 articles about 11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol 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: 85.0%

: 618-32-6
Benzoyl bromide

: 100311-70-4
3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5(Z)-undecene-1,2(R),3(S),11-tetrol

: 100311-71-5
11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1021/jo00356a004

Reference yield:

: 53036-80-9
6-carboxy hexylidene triphenylphosphorane

: 100311-71-5
11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol

Guidance literature:: Multi-step reaction with 4 steps

1: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / -78 - 20 °C

2: NaHCO₃ / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature

3: 68 percent / AlH₃*Et₂O / tetrahydrofuran / 0.5 h / 0 °C

4: 85 percent / Et₃N / CH₂Cl₂ / 0 °C

With aluminium hydride * diethyl ether; sodium hydrogencarbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/jo00356a004

Reference yield:

: 93292-42-3
2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

: 100311-71-5
11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol

Guidance literature:: Multi-step reaction with 4 steps

1: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / -78 - 20 °C

2: NaHCO₃ / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature

3: 68 percent / AlH₃*Et₂O / tetrahydrofuran / 0.5 h / 0 °C

4: 85 percent / Et₃N / CH₂Cl₂ / 0 °C

With aluminium hydride * diethyl ether; sodium hydrogencarbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/jo00356a004