(2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane

Base Information

Chemical Name:(2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane
CAS No.:201867-99-4
Molecular Formula:C₄₁H₆₉IO₅Si₃
Molecular Weight:853.157
Hs Code.:

(2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane

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

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

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

There total 16 articles about (2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-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: 98.0%

: Toluene-4-sulfonic acid (2R,4S,6R,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

: 201867-99-4
(2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: With 1H-imidazole; lithium iodide; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)10501-9

Reference yield:

: 127642-52-8
ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-2-propenoate

: 201867-99-4
(2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: Multi-step reaction with 11 steps

1: 96 percent / DIBAL / CH₂Cl₂

2: TBHP, (-)-DET, Ti(O-i-Pr)4 / CH₂Cl₂ / -20 °C

3: 93 percent / LiBH₄, Ti(O-i-Pr)4 / toluene / 0 °C

4: 93 percent / tosylimidazole, NaH / tetrahydrofuran / 0 °C

5: t-BuLi / diethyl ether / -78 deg C -> -45 deg C, 1 h; -78 deg C -> -25 deg C, 1 h

6: 65 percent / HMPA / diethyl ether / -78 deg C -> RT

7: 90 percent / TFA / CH₂Cl₂; H₂O / 0 °C

8: 88 percent / DMAP / CH₂Cl₂

9: Hg(ClO₄)2, CaCO₃ / acetonitrile; H₂O

10: 98 percent / 2,6-lutidine / CH₂Cl₂

11: 98 percent / LiI, imidazole / dimethylformamide

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium borohydride; mercury(II) perchlorate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; N-tosylimidazole; trifluoroacetic acid; calcium carbonate; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(97)10501-9

Reference yield:

: (S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propane-1,2-diol

: 201867-99-4
(2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / tosylimidazole, NaH / tetrahydrofuran / 0 °C

2: t-BuLi / diethyl ether / -78 deg C -> -45 deg C, 1 h; -78 deg C -> -25 deg C, 1 h

3: 65 percent / HMPA / diethyl ether / -78 deg C -> RT

4: 90 percent / TFA / CH₂Cl₂; H₂O / 0 °C

5: 88 percent / DMAP / CH₂Cl₂

6: Hg(ClO₄)2, CaCO₃ / acetonitrile; H₂O

7: 98 percent / 2,6-lutidine / CH₂Cl₂

8: 98 percent / LiI, imidazole / dimethylformamide

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; mercury(II) perchlorate; tert.-butyl lithium; sodium hydride; N-tosylimidazole; trifluoroacetic acid; calcium carbonate; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(97)10501-9