tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane

Base Information

• Chemical Name: tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane
• CAS No.: 154920-02-2
• Molecular Formula: C₂₃H₃₈O₃Si
• Molecular Weight: 390.638
• Mol file: 154920-02-2.mol

Synonyms:tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane

Chemical Property of tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane

There total 13 articles about tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-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: 98.0%

2,2-dimethoxy-propane (77-76-9) + (1R,2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-methylene-1-phenyl-hexane-1,3-diol (154920-00-0) → tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane (154920-02-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene;

DOI:10.1016/S0040-4039(00)61344-8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + 3-((4S,5S,6R)-2,2,5-Trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-en-1-ol (159734-12-0) → tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane (154920-02-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → tert-Butyl-dimethyl-[3-((4S,5S,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane (154920-02-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / CF₃SO₃H / cyclohexane / 0 - 20 °C

2.1: 60 percent / iPrMgBr / tetrahydrofuran / -10 °C

3.1: 92 percent / tBuLi / diethyl ether; hexane / -78 °C

4.1: 93 percent / Zn(BH₄)2 / diethyl ether / -78 - -30 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

6.1: BuLi / tetrahydrofuran / -78 - -30 °C

7.1: TBAF / tetrahydrofuran / 20 °C

8.1: p-TsOH / benzene / 20 °C

8.2: aq. HCl / tetrahydrofuran / 0 °C

9.1: imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; zinc(II) tetrahydroborate; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; isopropylmagnesium bromide; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; benzene; 6.1: ether <1,2> Wittig rearrangement;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

upstream raw materials:

2,2-dimethoxy-propane

(1R,2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-methylene-1-phenyl-hexane-1,3-diol

tert-butyldimethylsilyl chloride

3-((4S,5S,6R)-2,2,5-Trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-en-1-ol

Downstream raw materials:

(2R,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-methylene-1-phenyl-hexan-3-ol

(4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol

1-[(S)-4-Iodo-2-methylene-1-((R)-1-methyl-2-phenyl-ethyl)-butoxymethyl]-4-methoxy-benzene

tert-butyl-{3-[1-(4-methoxy-benzyloxy)-2-methyl-3-phenyl-propyl]-but-3-enyloxy}-dimethyl-silane