ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

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Chemical Name:ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate
CAS No.:627546-49-0
Molecular Formula:C₁₉H₂₈O₆
Molecular Weight:352.428
Hs Code.:

Synonyms:ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

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Chemical Property of ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

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Technology Process of ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

There total 3 articles about ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate 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: 92.0%

: 64-17-5
ethanol

: 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

: 627546-49-0
ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

Guidance literature:: With lithium thioethoxide; at 20 ℃;
DOI:10.1002/anie.200352509

Reference yield:

: 736140-94-6
(2E)-(5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-2-heptene-1-one

: 627546-49-0
ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 853 mg / Sm(O-iPr)3; (R)-H₈-BINOL; cumene hydroperoxide / toluene; tetrahydrofuran / 0.67 h / 25 °C

2: 94.5 percent / NaBH₄; PhSeSePh; AcOH / ethanol / 0.25 h / 25 °C

3: 92 percent / EtSLi / ethanol / 0.67 h / 25 °C

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

Reference yield:

: 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

: 627546-49-0
ethyl (3R,5R,6R)-7-benzyloxy-3-hydroxy-5,6-dihydroxy-5,6-O-isopropylideneheptanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 94.5 percent / NaBH₄; PhSeSePh; AcOH / ethanol / 0.25 h / 25 °C

2: 92 percent / EtSLi / ethanol / 0.67 h / 25 °C

With sodium tetrahydroborate; diphenyl diselenide; lithium thioethoxide; acetic acid; In ethanol;
DOI:10.1021/ja0485917