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

Base Information

Chemical Name:(4R,5S)-4-[(R)-1-Benzyloxy-3-(2,2-dimethyl-propionyloxy)-propyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester
CAS No.:199658-14-5
Molecular Formula:C₂₅H₃₄Cl₃NO₈
Molecular Weight:582.906
Hs Code.:

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

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

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

There total 12 articles about (4R,5S)-4-[(R)-1-Benzyloxy-3-(2,2-dimethyl-propionyloxy)-propyl]-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:

: 1027169-34-1
2,2-Dimethyl-propionic acid (R)-3-benzyloxy-4-oxo-butyl ester

: 199658-14-5
(4R,5S)-4-[(R)-1-Benzyloxy-3-(2,2-dimethyl-propionyloxy)-propyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

With hydrogenchloride; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; bis(acetylacetonate)oxovanadium; dimethylsulfide; water; diethylaluminium chloride; titanium tetrachloride; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4039(97)10077-6

Reference yield:

: 199658-08-7
2,2-Dimethyl-propionic acid (R)-3-benzyloxy-4-hydroxy-butyl ester

: 199658-14-5
(4R,5S)-4-[(R)-1-Benzyloxy-3-(2,2-dimethyl-propionyloxy)-propyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 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

With hydrogenchloride; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethylsulfide; water; diethylaluminium chloride; titanium tetrachloride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4039(97)10077-6

Reference yield:

: 199658-07-6
2,2-Dimethyl-propionic acid (R)-3-hydroxy-4-(4-methoxy-benzyloxy)-butyl ester

: 199658-14-5
(4R,5S)-4-[(R)-1-Benzyloxy-3-(2,2-dimethyl-propionyloxy)-propyl]-2,2-dimethyl-5-(2,2,2-trichloro-acetylamino)-[1,3]dioxane-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: Et₃N / tetrahydrofuran

2: Et₃SiH, TMSOTf / CH₂Cl₂ / -35 °C

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

4: TiCl₄ / CH₂Cl₂ / -78 °C

5: 98 percent / VO(acac), t-BuOOH / CH₂Cl₂ / -25 °C

6: 97 percent / DBU / CH₂Cl₂ / -20 °C

7: 73 percent / Et₂AlCl / hexane; CH₂Cl₂

8: 100 percent / HCl, H₂O

9: p-TsOH*H₂O / CH₂Cl₂

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

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

12: diethyl ether

With hydrogenchloride; triethylsilane; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; water; diethylaluminium chloride; titanium tetrachloride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4039(97)10077-6