(R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one

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Chemical Name:(R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one
CAS No.:627546-50-3
Molecular Formula:C₂₁H₂₇NO₅
Molecular Weight:373.449
Hs Code.:

Synonyms:(R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one

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Chemical Property of (R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one

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Technology Process of (R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one

There total 5 articles about (R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one 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: 94.5%

: 627546-46-7
(2S,3R,5R,6R)-7-benzyloxy-trans-2,3-epoxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-1-heptanone

: 627546-50-3
(R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one

Guidance literature:: With sodium tetrahydroborate; diphenyl diselenide; acetic acid; In ethanol;
DOI:10.1002/anie.200352509

Reference yield:

: 54582-33-1
1,1'-carbonyldiimidazole

: 627546-50-3
(R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: PhLi / tetrahydrofuran; diethyl ether / 1 h / 25 °C

1.2: 98 percent / tetrahydrofuran; diethyl ether / 25 °C

2.1: 86 percent / toluene / 36 h / 65 °C

3.1: 853 mg / Sm(O-iPr)3; (R)-H₈-BINOL; cumene hydroperoxide / toluene; tetrahydrofuran / 0.67 h / 25 °C

4.1: 94.5 percent / NaBH₄; PhSeSePh; AcOH / ethanol / 0.25 h / 25 °C

With sodium tetrahydroborate; Cumene hydroperoxide; diphenyl diselenide; samarium(III) isopropoxide; acetic acid; phenyllithium; (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol; In tetrahydrofuran; diethyl ether; ethanol; toluene; 2.1: Wittig olefination;
DOI:10.1021/ja0485917

Reference yield:

: 627546-31-0
1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone

: 627546-50-3
(R)-4-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-pyrrol-1-yl-butan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / toluene / 36 h / 65 °C

2: 853 mg / Sm(O-iPr)3; (R)-H₈-BINOL; cumene hydroperoxide / toluene; tetrahydrofuran / 0.67 h / 25 °C

3: 94.5 percent / NaBH₄; PhSeSePh; AcOH / ethanol / 0.25 h / 25 °C

With sodium tetrahydroborate; Cumene hydroperoxide; diphenyl diselenide; samarium(III) isopropoxide; acetic acid; (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol; In tetrahydrofuran; ethanol; toluene; 1: Wittig olefination;
DOI:10.1021/ja0485917