(2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

Base Information

Chemical Name:(2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol
CAS No.:262614-97-1
Molecular Formula:C₃₃H₄₉BrO₈Si
Molecular Weight:681.737
Hs Code.:

(2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

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Chemical Property of (2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

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Technology Process of (2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

There total 2 articles about (2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol 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:

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 262614-97-1
(2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / DIPEA; Bu₄NI / tetrahydrofuran / 24 h / 20 °C

2: 98 percent / Dibal-H / CH₂Cl₂ / 0.75 h / -78 °C

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Condensation / 2: Reduction;
DOI:10.1021/ol0000049

Reference yield:

: 194342-86-4
Acetic acid (2R,4S,6R,8S,10S)-8-[2-(2-bromo-benzyloxy)-ethyl]-10-hydroxy-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

: 262614-97-1
(2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / DIPEA; Bu₄NI / tetrahydrofuran / 24 h / 20 °C

2: 98 percent / Dibal-H / CH₂Cl₂ / 0.75 h / -78 °C

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Condensation / 2: Reduction;
DOI:10.1021/ol0000049

Reference yield:

: 262614-97-1
(2R,4S,6S,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-2-(4-methoxy-benzyloxymethyl)-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

: 262614-93-7
(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-2-((Z)-2-trimethylsilanyloxy-but-2-enyl)-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: Multi-step reaction with 10 steps

1.1: 96 percent / TPAP; NMO; 4 Angstroem MS / CH₂Cl₂ / 1 h / 20 °C

2.1: 93 percent / tetrahydrofuran; diethyl ether / 2.5 h / -78 - 0 °C

3.1: 93 percent / DIPEA / CH₂Cl₂ / -40 - 0 °C

4.1: 90 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

5.1: 82 percent / I₂; PPh₃; imidazole / benzene / 1.5 h / 20 °C

6.1: 100 percent / dimethylformamide / 36 h / 65 °C

7.1: (i-Pr₂)AlH / CH₂Cl₂ / 0.33 h / -78 °C

8.1: diethyl ether / 3 h / -78 - 9 °C

9.1: 99 percent / TPAP; NMP; 4 Angstroem MS / CH₂Cl₂ / 9 h / 20 °C

10.1: LiN(PhMe₂Si)2 / tetrahydrofuran / 1 h / -78 °C

10.2: 35 percent / tetrahydrofuran / 6 h / -78 - 20 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; N-methyl-2-indolinone; tetrapropylammonium perruthennate; lithium bis(dimethylphenylsilyl)amide; 4 Angstroem MS; water; iodine; diisopropyl aluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Oxidation / 2.1: Addition / 3.1: Condensation / 4.1: Hydrolysis / 5.1: Substitution / 6.1: Substitution / 7.1: Reduction / 8.1: Grignard reaction / 9.1: Oxidation / 10.1: Metallation / 10.2: Substitution;
DOI:10.1021/ol0000049