(2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol

Base Information

• Chemical Name: (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol
• CAS No.: 211988-85-1
• Molecular Formula: C₂₅H₄₂O₅Si
• Molecular Weight: 450.691
• Mol file: 211988-85-1.mol

Synonyms:(2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol

Chemical Property of (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol

There total 10 articles about (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol 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: 84.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + (2R,3Z,8S)-8-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-nonen-2-ol (211988-79-3) → (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol (211988-85-1)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(98)01078-8

Reference yield:

(4S)-4-[tert-butyl(dimethyl)silyl]oxypentyl 4-methylbenzenesulfonate (74500-59-7) → (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol (211988-85-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / lithium acetylide ethylenediamine / dimethylsulfoxide / 2 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

2.2: 81 percent / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: 95 percent / H₂; quinoline / 5percent Pd/CaCO₃ / methanol / 2 h

4.1: 99 percent / LiI; LiAlH₄ / diethyl ether / 0.5 h / -78 °C

5.1: 84 percent / camphorsulfonic acid / CH₂Cl₂ / 4 h / 20 °C

With quinoline; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; hydrogen; lithium acetylide-ethylenediamine complex; lithium iodide; 5percent Pd/CaCO₃; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 4.1: Suzuki reaction;

DOI:10.1021/jo0110855

Reference yield:

(S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-3-yn-2-one (211988-84-0) → (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol (211988-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / H₂; quinoline / 5percent Pd/CaCO₃ / methanol / 2 h

2: 99 percent / LiI; LiAlH₄ / diethyl ether / 0.5 h / -78 °C

3: 84 percent / camphorsulfonic acid / CH₂Cl₂ / 4 h / 20 °C

With quinoline; lithium aluminium tetrahydride; camphor-10-sulfonic acid; hydrogen; lithium iodide; 5percent Pd/CaCO₃; In methanol; diethyl ether; dichloromethane; 2: Suzuki reaction;

DOI:10.1021/jo0110855

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(2R,3Z,8S)-8-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-nonen-2-ol

(4S)-4-[tert-butyl(dimethyl)silyl]oxypentyl 4-methylbenzenesulfonate

(S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-3-yn-2-one

Downstream raw materials:

methyl 3-[(2R,4S,6R)-6-((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-2-(phenylsulfonyl)propanoate

(1R,2Z,7S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-[(2S)-5-oxo-4-(phenylsulfonyl)tetrahydro-2-furanyl]methyl-2-octenyl 4-methoxybenzoate

(1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one

(2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl-4-methylbenzenesulfonate