ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Base Information

Chemical Name:ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
CAS No.:478623-19-7
Molecular Formula:C₂₂H₃₃NO₇
Molecular Weight:423.507
Hs Code.:

Synonyms:ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

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Chemical Property of ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

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Technology Process of ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

There total 5 articles about ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 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: 72.0%

: 77-76-9
2,2-dimethoxy-propane

: 478623-18-6
ethyl (2R,3S,4R)-4-(tert-butoxycarbonyl)amino-2,3-dihydroxy-5-(4-methoxyphenyl)pentanoate

: 478623-19-7
ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃;
DOI:10.1055/s-2002-33904

Reference yield:

: 94790-24-6
(2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester

: 478623-19-7
ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / LiBH₄ / diethyl ether; methanol / 5 h / Heating

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -45 - 0 °C

3: 1.35 g / benzene / 15 h / 20 °C

4: 60 percent / AD-mix-α; (DHQ)2PHAL; aq. potassium osmate / 2-methyl-propan-2-ol / 18 h / 20 °C

5: 72 percent / CSA / CH₂Cl₂ / 20 °C

With potassium osmate(VI); AD-mix-α; lithium borohydride; Hydroquinone 1,4-phthalazinediyl diether; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; tert-butyl alcohol; benzene; 2: Swern oxidation / 3: Wittig reaction / 4: Sharpless asymmetric dihydroxylation;
DOI:10.1055/s-2002-33904

Reference yield:

: 120349-75-9
(2R)-2-(tert-butoxycarbonyl)amino-3-(4-methoxyphenyl)propan-1-ol

: 478623-19-7
ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -45 - 0 °C

2: 1.35 g / benzene / 15 h / 20 °C

3: 60 percent / AD-mix-α; (DHQ)2PHAL; aq. potassium osmate / 2-methyl-propan-2-ol / 18 h / 20 °C

4: 72 percent / CSA / CH₂Cl₂ / 20 °C

With potassium osmate(VI); AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; tert-butyl alcohol; benzene; 1: Swern oxidation / 2: Wittig reaction / 3: Sharpless asymmetric dihydroxylation;
DOI:10.1055/s-2002-33904