(4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

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Chemical Name:(4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one
CAS No.:176656-12-5
Molecular Formula:C₄₅H₆₈O₇Si₂
Molecular Weight:777.202
Hs Code.:

(4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

Synonyms:(4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

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Chemical Property of (4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

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Technology Process of (4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

There total 21 articles about (4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-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: 69.0%

: 176656-20-5
(4S,6R,9R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-ol

: 176656-12-5
(4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 0.5h;
DOI:10.1021/jo951646q

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 176656-12-5
(4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

Guidance literature:: Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂ / 12 h / 0 °C

2: NMO, OsO₄ / tetrahydrofuran / 1) 0 deg C -> 15 deg C, 10 h, 2) 25 deg C, 17 h

3: 93 percent / pyridine, DMAP / 0.5 h

4: 1) MsCl, DMAP, pyridine, 2) NaOMe / 1) 0 deg C, 3 h, 2) MeOH, 0 deg C, 1 h

5: 1) n-BuLi, 2) BF₃*Et₂O / 1) THF, -78 deg C, 15 min; -20 deg C, 15 min, 2) THF, -78 deg C, 30 min; -20 deg C, 12 h

6: 0.100 g / CSA / tetrahydrofuran; H₂O / 0.08 h

7: 1) m-CPBA, 2) p-TsOH*H₂O / 1) CH₂Cl₂, 0 deg C, 1.5 h, 2) CH₂Cl₂, 1 h

With pyridine; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo951646q

Reference yield:

: 143347-88-0
(R)-2,2-Dimethyl-4-((S)-1-methyl-allyl)-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

: 176656-12-5
(4S,6R)-4-{(E)-(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / L-Selectride / tetrahydrofuran / 0.75 h / -78 °C

2: 87 percent / imidazole / dimethylformamide / 25 h / Ambient temperature

3: 1) OsO₄, NMO, 2) NaIO₄ / 1) THF, H₂O, benzene, room temperature, 40 min, 2) THF, H₂O, benzene, 30 min

4: 1) t-BuLi / 1) Et₂O, pentane, -78 deg C, 20 min, 2) Et₂O, pentane, -78 deg C, 1 h

5: 76 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 69 percent / TBAF / tetrahydrofuran / 0.67 h / 0 °C

7: 69 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

With 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; tert.-butyl lithium; L-Selectride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo951646q