[(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

Base Information

Chemical Name:[(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
CAS No.:262614-99-3
Molecular Formula:C₃₂H₅₇BrO₇Si₂
Molecular Weight:689.875
Hs Code.:

[(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

Synonyms:[(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

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Chemical Property of [(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

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Technology Process of [(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

There total 7 articles about [(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 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 6 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

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

: 262614-99-3
[(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

Guidance literature:: Multi-step reaction with 6 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

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