(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

Base Information

Chemical Name:(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane
CAS No.:262614-85-7
Molecular Formula:C₃₂H₅₆BrIO₆Si₂
Molecular Weight:799.773
Hs Code.:

(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

Synonyms:(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

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Chemical Property of (2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

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Technology Process of (2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

There total 9 articles about (2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane 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: 82.0%

: 262614-99-3
[(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-methanol

: 262614-85-7
(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 20 ℃; for 1.5h;
DOI:10.1021/ol0000049

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 262614-85-7
(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / DIPEA / CH₂Cl₂ / -40 - 0 °C

2: 90 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

3: 82 percent / I₂; PPh₃; imidazole / benzene / 1.5 h / 20 °C

With 1H-imidazole; water; iodine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; benzene; 1: Condensation / 2: Hydrolysis / 3: Substitution;
DOI:10.1021/ol0000049

Reference yield:

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

: 262614-85-7
(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: Multi-step reaction with 7 steps

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

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

3: 96 percent / TPAP; NMO; 4 Angstroem MS / CH₂Cl₂ / 1 h / 20 °C

4: 93 percent / tetrahydrofuran; diethyl ether / 2.5 h / -78 - 0 °C

5: 93 percent / DIPEA / CH₂Cl₂ / -40 - 0 °C

6: 90 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

7: 82 percent / I₂; PPh₃; imidazole / benzene / 1.5 h / 20 °C

With 1H-imidazole; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; water; iodine; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Addition / 5: Condensation / 6: Hydrolysis / 7: Substitution;
DOI:10.1021/ol0000049