(E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Base Information

Chemical Name:(E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione
CAS No.:202406-73-3
Molecular Formula:C₃₄H₄₆O₇Si
Molecular Weight:594.821
Hs Code.:

(E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

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Chemical Property of (E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Chemical Property:

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Technology Process of (E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

There total 17 articles about (E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione 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:

: 111080-21-8
(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane

: 202406-73-3
(E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Guidance literature:: Multi-step reaction with 14 steps

1: 85 percent / nBuLi / tetrahydrofuran; hexane / -78 - -20 °C

2: 1.) (CF₃CO₂)2IPh; 2.) H₂O, AcOH / 1.) MeOH, 0 deg C; 2.) THF, r.t.

3: Me₄NBH(OAc)3 / acetic acid; acetonitrile / -40 - -20 °C

4: CSA / acetone / Ambient temperature

5: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) acetone, tBuOH, r.t.; 2.) H₂O, r.t.

6: LDA / tetrahydrofuran; hexane / -78 °C

7: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C -> 0 deg C

8: 89 percent / PPTS / methanol / 50 °C

9: imidazole / dimethylformamide / 0 °C

10: H₂ / Pd(OH)2/C / dioxane / Ambient temperature

11: DMSO, SO₃*Py, Et₃N / Ambient temperature

12: 98 percent

13: LiOH / tetrahydrofuran; methanol; H₂O / 50 - 75 °C

With 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; water; hydrogen; pyridinium p-toluenesulfonate; acetic acid; dimethyl sulfoxide; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1246/cl.1998.85

Reference yield:

: 909016-29-1
(3R,5S)-1-(benzyloxy)-2,2-dimethyloct-7-ene-3,5-diol

: 202406-73-3
(E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Guidance literature:: Multi-step reaction with 11 steps

1: CSA / acetone / Ambient temperature

2: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) acetone, tBuOH, r.t.; 2.) H₂O, r.t.

3: LDA / tetrahydrofuran; hexane / -78 °C

4: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C -> 0 deg C

5: 89 percent / PPTS / methanol / 50 °C

6: imidazole / dimethylformamide / 0 °C

7: H₂ / Pd(OH)2/C / dioxane / Ambient temperature

8: DMSO, SO₃*Py, Et₃N / Ambient temperature

9: 98 percent

10: LiOH / tetrahydrofuran; methanol; H₂O / 50 - 75 °C

With 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1246/cl.1998.85

Reference yield:

: 909016-28-0
(R)-8-Benzyloxy-6-hydroxy-7,7-dimethyl-oct-1-en-4-one

: 202406-73-3
(E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Guidance literature:: Multi-step reaction with 12 steps

1: Me₄NBH(OAc)3 / acetic acid; acetonitrile / -40 - -20 °C

2: CSA / acetone / Ambient temperature

3: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) acetone, tBuOH, r.t.; 2.) H₂O, r.t.

4: LDA / tetrahydrofuran; hexane / -78 °C

5: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C -> 0 deg C

6: 89 percent / PPTS / methanol / 50 °C

7: imidazole / dimethylformamide / 0 °C

8: H₂ / Pd(OH)2/C / dioxane / Ambient temperature

9: DMSO, SO₃*Py, Et₃N / Ambient temperature

10: 98 percent

11: LiOH / tetrahydrofuran; methanol; H₂O / 50 - 75 °C

With 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1246/cl.1998.85