(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

Base Information

• Chemical Name: (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
• CAS No.: 211988-77-1
• Molecular Formula: C₃₃H₄₆O₈SSi
• Molecular Weight: 630.875
• Mol file: 211988-77-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 13 articles about (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 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: 71.0%

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 (211988-80-6) → (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 (211988-77-1)

Guidance literature:

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; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 26h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 18h; Further stages.;

DOI:10.1021/jo0110855

Reference yield:

(4S)-4-[tert-butyl(dimethyl)silyl]oxypentyl 4-methylbenzenesulfonate (74500-59-7) → (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 (211988-77-1)

Guidance literature:

Multi-step reaction with 8 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

6.1: 99 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

7.1: NaH / various solvent(s); dimethylformamide / 0.5 h

7.2: 72 percent / dimethylformamide; various solvent(s) / 7 h / 100 °C

8.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 26 h / 20 °C

8.2: 71 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 18 h / 20 °C

With quinoline; dmap; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; hydrogen; lithium acetylide-ethylenediamine complex; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; 5percent Pd/CaCO₃; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 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) → (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 (211988-77-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / H₂; quinoline / 5percent Pd/CaCO₃ / methanol / 2 h

2.1: 99 percent / LiI; LiAlH₄ / diethyl ether / 0.5 h / -78 °C

3.1: 84 percent / camphorsulfonic acid / CH₂Cl₂ / 4 h / 20 °C

4.1: 99 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 5.5 h / 0 - 20 °C

5.1: NaH / various solvent(s); dimethylformamide / 0.5 h

5.2: 72 percent / dimethylformamide; various solvent(s) / 7 h / 100 °C

6.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 26 h / 20 °C

6.2: 71 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 18 h / 20 °C

With quinoline; dmap; lithium aluminium tetrahydride; camphor-10-sulfonic acid; hydrogen; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; 5percent Pd/CaCO₃; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Suzuki reaction;

DOI:10.1021/jo0110855

upstream 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

(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

(S)-(+)-6-((tert-butyldimethylsilyl)oxy)-1-heptyne

Downstream raw materials:

(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