tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

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Chemical Name:tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane
CAS No.:373645-83-1
Molecular Formula:C₄₄H₆₈O₆Si
Molecular Weight:721.106
Hs Code.:

tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

Synonyms:tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

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Chemical Property of tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

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Technology Process of tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

There total 29 articles about tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane 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: 93.0%

: 373645-66-0
(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

: 373645-83-1
tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2003.09.172

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 373645-83-1
tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

Guidance literature:: Multi-step reaction with 18 steps

1.1: triflic acid / diethyl ether / 2 h / 20 °C

2.1: 85 percent / i-PrMgCl / tetrahydrofuran / 0.5 h / -15 °C

3.1: 90 percent / tetrahydrofuran; diethyl ether / 2 h / 0 °C

4.1: Et₃N / diethyl ether / 1 h / 0 °C

5.1: diethyl ether / 21 h / -20 °C

5.2: 95 percent / 30percent aq. H₂O₂ / methanol / 0 - 20 °C / pH 7

6.1: 96 percent / SmI₂ / tetrahydrofuran / 1.5 h / -10 °C

7.1: 97 percent / K₂CO₃ / methanol; H₂O / 5 h / 20 °C

8.1: 94 percent / PPTS / toluene / 4 h / Heating

9.1: NaIO₄; NaHCO₃ / methanol; H₂O / 2 h / 20 °C

10.1: 82 percent / DBU; 1-(t-butyldimethylsiloxy)-1-methoxyethene / various solvent(s) / 8 h / Heating

11.1: 85 percent / methanol / 0 - 20 °C

12.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

13.1: 91 percent / aq. KOH / methanol / 1 h / Heating

14.1: 86 percent / DCC; 4-DMAP / CH₂Cl₂ / 16 h / 20 °C

15.1: LiTMP; LiBr / tetrahydrofuran / -100 °C

15.2: 81 percent / tetrahydrofuran / 0.08 h / -100 °C

16.1: 88 percent / LiAlH₄ / tetrahydrofuran / -78 - -10 °C

17.1: 95 percent / Et₃N / CH₂Cl₂ / 27 h / 20 °C

18.1: 66 percent / super-hydride; Et₃N / tetrahydrofuran / -10 - 20 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; samarium diiodide; trifluorormethanesulfonic acid; 2,2,6,6-tetramethylpiperidinyl-lithium; isopropylmagnesium chloride; ketene t-butyldimethylsilyl methyl acetal; pyridinium p-toluenesulfonate; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 6.1: Evans-Tischenko reaction / 10.1: Claisen rearrangement;
DOI:10.1021/ja011211m

Reference yield:

: 182193-69-7
(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one

: 373645-83-1
tert-Butyl-{(Z)-(1R,2S)-5-{(2R,3R)-2-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-oxetan-3-yl}-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2,4-dimethyl-pent-3-enyloxy}-dimethyl-silane

Guidance literature:: Multi-step reaction with 15 steps

1.1: Et₃N / diethyl ether / 1 h / 0 °C

2.1: diethyl ether / 21 h / -20 °C

2.2: 95 percent / 30percent aq. H₂O₂ / methanol / 0 - 20 °C / pH 7

3.1: 96 percent / SmI₂ / tetrahydrofuran / 1.5 h / -10 °C

4.1: 97 percent / K₂CO₃ / methanol; H₂O / 5 h / 20 °C

5.1: 94 percent / PPTS / toluene / 4 h / Heating

6.1: NaIO₄; NaHCO₃ / methanol; H₂O / 2 h / 20 °C

7.1: 82 percent / DBU; 1-(t-butyldimethylsiloxy)-1-methoxyethene / various solvent(s) / 8 h / Heating

8.1: 85 percent / methanol / 0 - 20 °C

9.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

10.1: 91 percent / aq. KOH / methanol / 1 h / Heating

11.1: 86 percent / DCC; 4-DMAP / CH₂Cl₂ / 16 h / 20 °C

12.1: LiTMP; LiBr / tetrahydrofuran / -100 °C

12.2: 81 percent / tetrahydrofuran / 0.08 h / -100 °C

13.1: 88 percent / LiAlH₄ / tetrahydrofuran / -78 - -10 °C

14.1: 95 percent / Et₃N / CH₂Cl₂ / 27 h / 20 °C

15.1: 66 percent / super-hydride; Et₃N / tetrahydrofuran / -10 - 20 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; samarium diiodide; 2,2,6,6-tetramethylpiperidinyl-lithium; ketene t-butyldimethylsilyl methyl acetal; pyridinium p-toluenesulfonate; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 3.1: Evans-Tischenko reaction / 7.1: Claisen rearrangement;
DOI:10.1021/ja011211m