(R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid

Base Information

Chemical Name:(R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid
CAS No.:146467-12-1
Molecular Formula:C₃₂H₃₇NO₇
Molecular Weight:547.648
Hs Code.:

Synonyms:(R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid

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Chemical Property of (R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid

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Technology Process of (R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid

There total 13 articles about (R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic 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: 83.0%

: 146467-11-0
[(1S,2S)-1-((4R,5R)-2,2-Dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl]-carbamic acid tert-butyl ester

: 146467-12-1
(R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile;
DOI:10.1021/jo00054a007

Reference yield:

: 146467-07-4
1-benzyl-3S-hydroxy-4R-[1'R,2'R-O-isopropylidene-3'-hydroxy]propyl-azetidin-2-one

: 146467-12-1
(R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / Et₃N / CH₂Cl₂ / -30 - 0 °C

2: 80 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 95 percent / ammonium formate / 10 percent Pd/C / ethane-1,2-diol / 0.05 h / microwave irradiation

4: 83 percent / NaOH / dioxane / 0 - 20 °C

5: 83 percent / aq. NaIO₄; RuCl₃ / acetonitrile; CCl₄ / 6 h / 20 °C

With ruthenium trichloride; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; ammonium formate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; ethylene glycol; acetonitrile; 1: Substitution / 2: Reduction / 3: Hydrogenolysis / 4: Acylation / 5: Oxidation;
DOI:10.1016/S0040-4020(00)00410-5

Reference yield:

: 146467-04-1
1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3'R,4'-dihydroxy]butyl azetidin-2-one

: 146467-12-1
(R)-tert-Butoxycarbonylamino-((4R,5R)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-acetic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / aq. NaIO₄ / methanol / 1.25 h / 0 - 5 °C

2: 90 percent / NaBH₄ / methanol / 1 h / 0 - 5 °C

3: 90 percent / ammonium formate / 10 percent Pd/C / ethane-1,2-diol / 0.05 h / microwave irradiation

4: 80 percent / Et₃N / CH₂Cl₂ / -30 - 0 °C

5: 80 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

6: 95 percent / ammonium formate / 10 percent Pd/C / ethane-1,2-diol / 0.05 h / microwave irradiation

7: 83 percent / NaOH / dioxane / 0 - 20 °C

8: 83 percent / aq. NaIO₄; RuCl₃ / acetonitrile; CCl₄ / 6 h / 20 °C

With ruthenium trichloride; sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; ammonium formate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; ethylene glycol; acetonitrile; 1: Oxidation / 2: Reduction / 3: Hydrogenolysis / 4: Substitution / 5: Reduction / 6: Hydrogenolysis / 7: Acylation / 8: Oxidation;
DOI:10.1016/S0040-4020(00)00410-5