2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

Base Information

Chemical Name:2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane
CAS No.:389085-87-4
Molecular Formula:C₅₉H₉₂O₉Si₃
Molecular Weight:1029.63
Hs Code.:

2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

Synonyms:2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

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Chemical Property of 2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

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Technology Process of 2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

There total 35 articles about 2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane 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: 68.0%

: 389085-88-5
1-[10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyl)oxy-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-5-(tert-butyldimethylsilyl)oxy-5-[5-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylpentan-2-one

: 389085-87-4
2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; for 5h;
DOI:10.1021/ol0168364

Reference yield:

: 26685-74-5
1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose

: 389085-87-4
2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 0 °C

2.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

3.1: 98 percent / benzene / 32 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

5.1: ozone / CH₂Cl₂ / 0.25 h / -78 °C

5.2: Me₂S / CH₂Cl₂ / 10 h / 20 °C

6.1: LiHMDS / hexane; tetrahydrofuran / 2 h / -78 °C

7.1: Ac₂O; pyridine / 5 h

7.2: 9.6 mg / DBU / CH₂Cl₂ / 2 h / 0 °C

8.1: 73 percent / BF₃*Et₂O / tetrahydrofuran / 2 h / -78 °C

9.1: 62 percent / CSA / CH₂Cl₂ / 5 h

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; ozone; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Wittig reaction;
DOI:10.1016/S0040-4020(02)01380-7

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 389085-87-4
2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 0 °C

2.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

3.1: 98 percent / benzene / 32 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

5.1: ozone / CH₂Cl₂ / 0.25 h / -78 °C

5.2: Me₂S / CH₂Cl₂ / 10 h / 20 °C

6.1: LiHMDS / hexane; tetrahydrofuran / 2 h / -78 °C

7.1: Ac₂O; pyridine / 5 h

7.2: 9.6 mg / DBU / CH₂Cl₂ / 2 h / 0 °C

8.1: 73 percent / BF₃*Et₂O / tetrahydrofuran / 2 h / -78 °C

9.1: 62 percent / CSA / CH₂Cl₂ / 5 h

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; ozone; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Wittig reaction;
DOI:10.1016/S0040-4020(02)01380-7