1-[(2S,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]-butan-2-ol

Base Information

Chemical Name:1-[(2S,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]-butan-2-ol
CAS No.:262614-86-8
Molecular Formula:C₃₅H₆₃BrO₇Si₂
Molecular Weight:731.956
Hs Code.:

1-[(2S,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]-butan-2-ol

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Chemical Property of 1-[(2S,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]-butan-2-ol

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Technology Process of 1-[(2S,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]-butan-2-ol

There total 12 articles about 1-[(2S,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]-butan-2-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:

: 925-90-6
ethylmagnesium bromide

: 1025954-24-8
[(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]-acetaldehyde

: 262614-86-8
1-[(2S,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]-butan-2-ol

Guidance literature:: In diethyl ether; at -78 - 9 ℃; for 3h;
DOI:10.1021/ol0000049

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 262614-86-8
1-[(2S,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]-butan-2-ol

Guidance literature:: Multi-step reaction with 6 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

4: 100 percent / dimethylformamide / 36 h / 65 °C

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

6: diethyl ether / 3 h / -78 - 9 °C

With 1H-imidazole; water; iodine; diisopropyl aluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Condensation / 2: Hydrolysis / 3: Substitution / 4: Substitution / 5: Reduction / 6: Grignard reaction;
DOI:10.1021/ol0000049

Reference yield:

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

: 262614-86-8
1-[(2S,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]-butan-2-ol

Guidance literature:: Multi-step reaction with 10 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

8: 100 percent / dimethylformamide / 36 h / 65 °C

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

10: diethyl ether / 3 h / -78 - 9 °C

With 1H-imidazole; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; water; iodine; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; 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: Condensation / 2: Reduction / 3: Oxidation / 4: Addition / 5: Condensation / 6: Hydrolysis / 7: Substitution / 8: Substitution / 9: Reduction / 10: Grignard reaction;
DOI:10.1021/ol0000049