(4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester

Base Information

• Chemical Name: (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester
• CAS No.: 199658-16-7
• Molecular Formula: C₃₆H₅₄Cl₃NO₈
• Molecular Weight: 735.186

Synonyms:

Chemical Property of (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester

There total 13 articles about (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester 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: 26.0%

7-(2-n-hexyl-1,3-dioxolan-2-yl)-n-heptyl-triphenylphosphonium bromide (78009-99-1) + (4R,5S)-4-((R)-1-Benzyloxy-3-oxo-propyl)-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester (199658-15-6) → (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-5-(2,2-dichloro-acetylamino)-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid methyl ester + (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester (199658-16-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4039(97)10077-6

Reference yield:

2,2-Dimethyl-propionic acid (R)-3-benzyloxy-4-oxo-butyl ester (1027169-34-1) → (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester (199658-16-7)

Guidance literature:

Multi-step reaction with 12 steps

1: TiCl₄ / CH₂Cl₂ / -78 °C

2: 98 percent / VO(acac), t-BuOOH / CH₂Cl₂ / -25 °C

3: 97 percent / DBU / CH₂Cl₂ / -20 °C

4: 73 percent / Et₂AlCl / hexane; CH₂Cl₂

5: 100 percent / HCl, H₂O

6: p-TsOH*H₂O / CH₂Cl₂

7: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C

8: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

9: diethyl ether

10: NaOMe / methanol

11: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 - 25 °C

12: 48 percent / nBuLi / hexane; tetrahydrofuran

With hydrogenchloride; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethylsulfide; water; sodium methylate; diethylaluminium chloride; titanium tetrachloride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(97)10077-6

Reference yield:

2,2-Dimethyl-propionic acid (R)-3-benzyloxy-4-hydroxy-butyl ester (199658-08-7) → (4R,5S)-4-[(E)-(R)-1-Benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester (199658-16-7)

Guidance literature:

Multi-step reaction with 13 steps

1: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 - 25 °C

2: TiCl₄ / CH₂Cl₂ / -78 °C

3: 98 percent / VO(acac), t-BuOOH / CH₂Cl₂ / -25 °C

4: 97 percent / DBU / CH₂Cl₂ / -20 °C

5: 73 percent / Et₂AlCl / hexane; CH₂Cl₂

6: 100 percent / HCl, H₂O

7: p-TsOH*H₂O / CH₂Cl₂

8: 1.) O₃; 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C

9: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

10: diethyl ether

11: NaOMe / methanol

12: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 - 25 °C

13: 48 percent / nBuLi / hexane; tetrahydrofuran

With hydrogenchloride; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethylsulfide; water; sodium methylate; diethylaluminium chloride; titanium tetrachloride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(97)10077-6

upstream raw materials:

7-(2-n-hexyl-1,3-dioxolan-2-yl)-n-heptyl-triphenylphosphonium bromide

(4R,5S)-4-((R)-1-Benzyloxy-3-oxo-propyl)-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester

2,2-Dimethyl-propionic acid (R)-3-benzyloxy-4-hydroxy-butyl ester

2,2-Dimethyl-propionic acid (R)-3-benzyloxy-4-oxo-butyl ester

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