(1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

Base Information

Chemical Name:(1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol
CAS No.:157687-06-4
Molecular Formula:C₂₈H₃₈O₄Si
Molecular Weight:466.693
Hs Code.:

Synonyms:(1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

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Chemical Property of (1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

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Technology Process of (1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

There total 15 articles about (1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-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: 85.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 157807-86-8
(1R,3S,4S,5R,6R,8R)-3-Ethoxy-5-hydroxymethyl-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

: 157687-06-4
(1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1021/jo00094a009

Reference yield:

: 61243-08-1
Acetic acid (2S,3S,6S)-6-ethoxy-2-iodomethyl-3,6-dihydro-2H-pyran-3-yl ester

: 157687-06-4
(1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 89 percent / AIBN / toluene

2: 100 percent / NEt₃, H₂O / methanol

3: NEt₃ / CH₂Cl₂

4: Bu₃SnCl, NaCNBH₃, AIBN

5: 78 percent / H₂O₂, KHCO₃, KF

7: 1.) O₃, 2.) Me₂S / 1.) MeOH

8: K₂CO₃ / methanol / 24 h

9: KHMDS

10: 78 percent / Bu₂SnO, NBS

11: 88 percent / NaBH(OAc)3 / ethyl acetate

12: 85 percent / NEt₃, DMAP / CH₂Cl₂

With dmap; potassium fluoride; N-Bromosuccinimide; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tributyltin chloride; water; dihydrogen peroxide; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium carbonate; potassium hydrogencarbonate; ozone; triethylamine; In methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo00094a009

Reference yield:

: 61243-02-5
Acetic acid (2R,3S,6S)-6-ethoxy-2-(toluene-4-sulfonyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester

: 157687-06-4
(1R,3S,4S,5R,6R,8R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethoxy-8-vinyl-2-oxa-bicyclo[2.2.2]octan-6-ol

Guidance literature:: Multi-step reaction with 13 steps

1: 89 percent / NaI, Ac₂O / 60 °C

2: 89 percent / AIBN / toluene

3: 100 percent / NEt₃, H₂O / methanol

4: NEt₃ / CH₂Cl₂

5: Bu₃SnCl, NaCNBH₃, AIBN

6: 78 percent / H₂O₂, KHCO₃, KF

8: 1.) O₃, 2.) Me₂S / 1.) MeOH

9: K₂CO₃ / methanol / 24 h

10: KHMDS

11: 78 percent / Bu₂SnO, NBS

12: 88 percent / NaBH(OAc)3 / ethyl acetate

13: 85 percent / NEt₃, DMAP / CH₂Cl₂

With dmap; potassium fluoride; N-Bromosuccinimide; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tributyltin chloride; water; dihydrogen peroxide; acetic anhydride; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium carbonate; potassium hydrogencarbonate; ozone; triethylamine; sodium iodide; In methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo00094a009