ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate

Base Information

Chemical Name:ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate
CAS No.:736141-18-7
Molecular Formula:C₂₀H₃₀O₆
Molecular Weight:366.455
Hs Code.:

Synonyms:ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate

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

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

There total 3 articles about ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate 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:

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

: 736141-18-7
ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate

Guidance literature:: Multi-step reaction with 4 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

4: 93 percent / Ag₂O / toluene / 36 h / 45 °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; silver(l) oxide; In tetrahydrofuran; ethanol; toluene;
DOI:10.1021/ja0485917

Reference yield:

: 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

: 736141-18-7
ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / EtSLi / ethanol / 0.67 h / 25 °C

2: 93 percent / Ag₂O / toluene / 36 h / 45 °C

With lithium thioethoxide; silver(l) oxide; In 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

: 736141-18-7
ethyl (3R,5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-3-methoxyheptanoate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 93 percent / Ag₂O / toluene / 36 h / 45 °C

With sodium tetrahydroborate; diphenyl diselenide; lithium thioethoxide; acetic acid; silver(l) oxide; In ethanol; toluene;
DOI:10.1021/ja0485917