3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid

Base Information

Chemical Name:3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid
CAS No.:301180-87-0
Molecular Formula:C₂₂H₃₁NO₇
Molecular Weight:421.491
Hs Code.:

3-(4-benzyl-2-<i>tert</i>-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-<i>tert</i>-butoxycarbonylamino-propionic acid

Synonyms:3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid

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Chemical Property of 3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid

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Technology Process of 3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid

There total 9 articles about 3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid 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: 78.0%

: 301180-86-9
[2-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

: 301180-87-0
3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1021/ol006246q DOI:10.1021/ol006246q

Reference yield:

: 828-01-3,7326-19-4,20312-36-1,156-05-8
D-phenyllactic acid

: 301180-87-0
3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / BF₃*OEt₂ / diethyl ether / 2 h / -20 °C

2.1: 77 percent / LDA / tetrahydrofuran / 2 h / -78 °C

3.1: NaH; CS₂; MeI / tetrahydrofuran

3.2: n-Bu₃SnH; AIBN / toluene / 2 h / Heating

4.1: 77 percent / PPTS / ethanol; H₂O / 6 h / Heating

5.1: 78 percent / PDC / dimethylformamide / 24 h / 20 °C

With carbon disulfide; dipyridinium dichromate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; diethyl ether; ethanol; water; N,N-dimethyl-formamide; 1.1: Cyclization / 2.1: Condensation / 3.1: Metallation / 3.2: Reduction / 4.1: Hydrolysis / 5.1: Oxidation;
DOI:10.1021/ol006246q DOI:10.1021/ol006246q

Reference yield:

: 301180-85-8
4-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 301180-87-0
3-(4-benzyl-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 77 percent / PPTS / ethanol; H₂O / 6 h / Heating

2: 78 percent / PDC / dimethylformamide / 24 h / 20 °C

With dipyridinium dichromate; pyridinium p-toluenesulfonate; In ethanol; water; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Oxidation;
DOI:10.1021/ol006246q DOI:10.1021/ol006246q