(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

Base Information

Chemical Name:(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane
CAS No.:346708-32-5
Molecular Formula:C₃₂H₅₄O₅Si
Molecular Weight:546.863
Hs Code.:

(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

Synonyms:(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

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Chemical Property of (1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

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Technology Process of (1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

There total 10 articles about (1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane 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:

: 160238-46-0
(2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal

: 346708-32-5
(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 10 steps

1.1: LDA / tetrahydrofuran / -78 °C

2.1: DIBAL-H / diethyl ether / 0 °C

3.1: pyridine / 0 °C

4.1: 95 percent / CH₂Cl₂ / 0 °C

5.1: (c-hex)2BCl; Et₃N / diethyl ether / -78 - 0 °C

5.2: diethyl ether / -78 - -20 °C

6.1: Et₂BOMe; NaBH₄ / methanol; tetrahydrofuran / -78 °C

7.1: 100 percent / PPTS / CH₂Cl₂ / 0 - 20 °C

8.1: 72 percent / 10 percent NaOH / methanol / 8 h / Heating

9.1: 85 percent / pyridine / CH₂Cl₂ / 0 °C

10.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

10.2: 93 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4.1: Dess-Martin periodinane oxidation / 5.1: Paterson reaction / 9.1: Dess-Martin periodinane oxidation / 10.2: Wittig reaction;
DOI:10.1016/S0040-4039(01)00401-4

Reference yield:

: 346708-20-1
(2R,3R/S)-1-(p-methoxybenzyloxy)-2-methylpentane-3,5-diol

: 346708-32-5
(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridine / 0 °C

2.1: 95 percent / CH₂Cl₂ / 0 °C

3.1: (c-hex)2BCl; Et₃N / diethyl ether / -78 - 0 °C

3.2: diethyl ether / -78 - -20 °C

4.1: Et₂BOMe; NaBH₄ / methanol; tetrahydrofuran / -78 °C

5.1: 100 percent / PPTS / CH₂Cl₂ / 0 - 20 °C

6.1: 72 percent / 10 percent NaOH / methanol / 8 h / Heating

7.1: 85 percent / pyridine / CH₂Cl₂ / 0 °C

8.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

8.2: 93 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.1: Dess-Martin periodinane oxidation / 3.1: Paterson reaction / 7.1: Dess-Martin periodinane oxidation / 8.2: Wittig reaction;
DOI:10.1016/S0040-4039(01)00401-4

Reference yield:

: (R)-3-Hydroxy-5-(4-methoxy-benzyloxy)-4-methyl-pentanoic acid methyl ester

: 346708-32-5
(1'E,1''R,3'S,4S,4'Z,5S,6S)-5-(tert-butyldimethylsilyloxymethyl)-4-(1',3'-dimethylhexa-1',4'-dienyl)-6-[2''-(p-methoxybenzyloxy)-1''-methylethyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 9 steps

1.1: DIBAL-H / diethyl ether / 0 °C

2.1: pyridine / 0 °C

3.1: 95 percent / CH₂Cl₂ / 0 °C

4.1: (c-hex)2BCl; Et₃N / diethyl ether / -78 - 0 °C

4.2: diethyl ether / -78 - -20 °C

5.1: Et₂BOMe; NaBH₄ / methanol; tetrahydrofuran / -78 °C

6.1: 100 percent / PPTS / CH₂Cl₂ / 0 - 20 °C

7.1: 72 percent / 10 percent NaOH / methanol / 8 h / Heating

8.1: 85 percent / pyridine / CH₂Cl₂ / 0 °C

9.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

9.2: 93 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.1: Dess-Martin periodinane oxidation / 4.1: Paterson reaction / 8.1: Dess-Martin periodinane oxidation / 9.2: Wittig reaction;
DOI:10.1016/S0040-4039(01)00401-4