(1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde

Base Information

Chemical Name:(1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde
CAS No.:1026543-82-7
Molecular Formula:C₂₇H₃₆O₄Si
Molecular Weight:452.666
Hs Code.:

Synonyms:(1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde

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Chemical Property of (1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde

Chemical Property:

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Technology Process of (1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde

There total 17 articles about (1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde 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:

: 157687-07-5
(3S,5R,6R,8R)-3-Ethoxy-5-<<(tert-butyldiphenylsilyl)oxy>methyl>-6-methoxy-8-vinyl-2-oxabicyclo<2.2.2>octane

: 1026543-82-7
(1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde

Guidance literature:: With acetic acid; In tetrahydrofuran; at 90 ℃; for 12h;
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

: 1026543-82-7
(1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 14 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

13: 82 percent / Ag₂O

14: aq. CH₃COOH / tetrahydrofuran / 12 h / 90 °C

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; acetic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; 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

: 1026543-82-7
(1S,2R,3R,4R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-6-vinyl-cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 15 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

14: 82 percent / Ag₂O

15: aq. CH₃COOH / tetrahydrofuran / 12 h / 90 °C

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; acetic acid; triethylamine; sodium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo00094a009