(3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Base Information

Chemical Name:(3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one
CAS No.:327027-84-9
Molecular Formula:C₄₄H₆₄O₅Si₂
Molecular Weight:729.16
Hs Code.:

(3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Synonyms:(3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

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Chemical Property of (3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

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Technology Process of (3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

There total 24 articles about (3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one 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: 65.0%

: 75-11-6
diiodomethane

: 327027-83-8
(3Z,9E)-(1R,7S,11S,15R,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-triene-5,13-dione

: 327027-84-9
(3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: With titanium tetrachloride; lead(II) iodide; zinc; In tetrahydrofuran; at -10 - 20 ℃;
DOI:10.1021/ol000342+

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 327027-84-9
(3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

2: DIBAL / CH₂Cl₂ / -78 °C

3: Dess-Martin periodinane

4: NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol

5: 77 percent / DDQ / CH₂Cl₂ / pH 7

6: DEAD; PPh₃ / benzene / 20 °C

7: 72 percent / diethyl ether / -10 °C

8: 65 percent / Zn; PbI₂; TiCl₄ / tetrahydrofuran / -10 - 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lead(II) iodide; zinc; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol; benzene; 6: Mitsunobu macrolactonization;
DOI:10.1021/ol000342+

Reference yield:

: 124655-05-6
(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

: 327027-84-9
(3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: TfOH / diethyl ether

2.1: DIBAL / CH₂Cl₂ / -100 °C

3.1: i-Pr₂NEt; LiCl / acetonitrile / 20 °C

4.1: DIBAL / CH₂Cl₂ / -78 °C

4.2: Dess-Martin periodinane

5.1: (+)-Ipc₂BCl; Et₃N / diethyl ether

5.2: diethyl ether / -100 °C

6.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

7.1: DIBAL / CH₂Cl₂ / -78 °C

8.1: Dess-Martin periodinane

9.1: NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol

10.1: DDQ / CH₂Cl₂ / pH 7

11.1: 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / toluene / 20 °C

12.1: 72 percent / diethyl ether / -10 °C

13.1: 65 percent / Zn; PbI₂; TiCl₄ / tetrahydrofuran / -10 - 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; (+)-β-chlorodiisopinocampheylborane; 2-methyl-but-2-ene; trifluorormethanesulfonic acid; 2,4,6-trichlorobenzoyl chloride; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lead(II) iodide; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 3.1: Masamune-Roush HWE reaction;
DOI:10.1021/ol000342+