[(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester
CAS No.:138253-28-8
Molecular Formula:C₂₁H₃₂N₂O₆
Molecular Weight:408.495
Hs Code.:

Synonyms:[(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester

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Chemical Property of [(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester

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Technology Process of [(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester

There total 11 articles about [(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl 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:

: 17342-08-4
(S)-Pyroglutaminol

: 138253-28-8
[(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 73 percent / NaH / dimethylsulfoxide / 24 h / Ambient temperature

2: DDQ / CH₂Cl₂; H₂O / 4 h / Ambient temperature

3: NaH / tetrahydrofuran / 1 h / Ambient temperature

4: 1) LDA / 1) 2) THF, -78 deg C, 30 min

5: 30percent aq. H₂O₂ / ethyl acetate / 0.5 h / Ambient temperature

6: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; toluene / 12.5 h / Ambient temperature

7: p-TsOH*H₂O / 5 h / Ambient temperature

8: ceric ammonium nitrate / acetonitrile; H₂O / 1) 0 deg C, 20 min 2) r.t., 1.5h

9: 4-(N,N-dimethylamino)pyridine / acetonitrile / 10 h / Ambient temperature

10: LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11: diphenyl phosphorazidate, Et₃N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.

With dmap; lithium hydroxide; osmium(VIII) oxide; ammonium cerium(IV) nitrate; diphenyl phosphoryl azide; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)79444-5

Reference yield:

: 152500-26-0
(S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone

: 138253-28-8
[(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: NaH / tetrahydrofuran / 1 h / Ambient temperature

2: 1) LDA / 1) 2) THF, -78 deg C, 30 min

3: 30percent aq. H₂O₂ / ethyl acetate / 0.5 h / Ambient temperature

4: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; toluene / 12.5 h / Ambient temperature

5: p-TsOH*H₂O / 5 h / Ambient temperature

6: ceric ammonium nitrate / acetonitrile; H₂O / 1) 0 deg C, 20 min 2) r.t., 1.5h

7: 4-(N,N-dimethylamino)pyridine / acetonitrile / 10 h / Ambient temperature

8: LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

9: diphenyl phosphorazidate, Et₃N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.

With dmap; lithium hydroxide; osmium(VIII) oxide; ammonium cerium(IV) nitrate; diphenyl phosphoryl azide; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)79444-5

Reference yield:

: 138253-25-5
(S)-1-(4'-methoxybenzyl)-5-methoxymethyl-pyrrolidin-2-one

: 138253-28-8
[(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1) LDA / 1) 2) THF, -78 deg C, 30 min

2: 30percent aq. H₂O₂ / ethyl acetate / 0.5 h / Ambient temperature

3: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; toluene / 12.5 h / Ambient temperature

4: p-TsOH*H₂O / 5 h / Ambient temperature

5: ceric ammonium nitrate / acetonitrile; H₂O / 1) 0 deg C, 20 min 2) r.t., 1.5h

6: 4-(N,N-dimethylamino)pyridine / acetonitrile / 10 h / Ambient temperature

7: LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

8: diphenyl phosphorazidate, Et₃N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.

With dmap; lithium hydroxide; osmium(VIII) oxide; ammonium cerium(IV) nitrate; diphenyl phosphoryl azide; dihydrogen peroxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)79444-5